Highly active and selective catalysts for the formation of α-aryl ketones

Journal of the American Chemical Society

Volumn 122, Issue 7, 2000, Pages 1360-1370

  Fox, Joseph M ^a   Huang, Xiaohua ^a   Chieffi, André ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; KETONE DERIVATIVE; MALONIC ACID DERIVATIVE; NITROALKANE; PALLADIUM; POTASSIUM DIHYDROGEN PHOSPHATE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; REACTION ANALYSIS;

EID: 0033997284     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993912d     Document Type: Article

References (115)

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9. For related reactions that are believed to involve aryl radicals as intermediates, see: (a) Sakakura, T.; Hara, M.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1985, 1545. (b) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1993, 49, 235. Kende, A. S.; Koch, K.; Smith, C. A. J. Am. Chem. Soc. 1988, 110, 2210.
10. For related reactions that are believed to involve aryl radicals as intermediates, see: (a) Sakakura, T.; Hara, M.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1985, 1545. (b) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1993, 49, 235. Kende, A. S.; Koch, K.; Smith, C. A. J. Am. Chem. Soc. 1988, 110, 2210.
11. For related reactions that are believed to involve aryl radicals as intermediates, see: (a) Sakakura, T.; Hara, M.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1985, 1545. (b) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1993, 49, 235. Kende, A. S.; Koch, K.; Smith, C. A. J. Am. Chem. Soc. 1988, 110, 2210.
12. For a tabular survey, see ref 6b, page 464.
13. RN 1 reaction. For illustrative examples of solvent effects, see ref 6b and (a) Moon, M. P.; Wolfe, J. F. J. Org. Chem. 1979, 44, 4081. (b) Semmelhack, M. F.; Barger, T. J. Am. Chem. Soc. 1980, 102, 7765.
14. RN 1 reaction. For illustrative examples of solvent effects, see ref 6b and (a) Moon, M. P.; Wolfe, J. F. J. Org. Chem. 1979, 44, 4081. (b) Semmelhack, M. F.; Barger, T. J. Am. Chem. Soc. 1980, 102, 7765.
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16. (b) Hay, J. V.; Wolfe, J. F. J. Am. Chem. Soc. 1975, 97, 3702.
17. (c) Komin, A. P.; Wolfe, J. F. J. Org. Chem. 1977, 42, 2481.
18. (d) Beugelmans, R. ; Ginsburg, H. J. Chem. Soc., Chem. Commun. 1980, 508.
19. (e) Bard, R. R.; Bunnett, J. F. J. Org. Chem. 1980, 45, 1546.
20. (f) Beugelmans, R.; Boudet, B.; Quintero, L. Tetrahedron Lett. 1980, 21, 1943.
21. (g) Beugelmans, R.; Ginsburg, H. Heterocycles 1985, 23, 1197.
22. (h) Beugelmans, R.; Bois-Choussy, M. Synthesis 1981, 729.
23. Wolfe, J. F.; Moon, M. P.; Sleevi, M. C.; Bunnett, J. F.; Bard, R. R. J. Org. Chem. 1978, 43, 1020.
24. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
25. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
26. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
27. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
28. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
29. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
30. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
31. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)-chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
32. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
33. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
34. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
35. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
36. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
37. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
38. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
39. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
40. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
41. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
42. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
43. Reagents that produce a-aryl ketones: Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673. (c) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (d) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061. Organobismuth reagents: (e) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein. (f) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039 and references therein. Organoboron reagents: (g) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein. Tricarbonylcydohexadienylium iron salts: (h) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)- chromium tricarbonyl: (i) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241. Copper reagents: (j) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697. (k) Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165 and references therein. (l) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc. 1975, 97, 7372. (m) Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325. Aryldiazonium salts with catalytic CuCl: (n) Al Adel, I.; Adeoti Salami, B.; Levisalles, J.; Rudler, H. Bull. Soc. Chim. Fr. 1976, 930. Aryl lead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II, McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein. (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein. (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)nickel bromide: (r) Hegedus, L. S.; Stiverson, R. K. J. Am. Chem. Soc. 1974, 96, 3250. Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550. Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
44. For reagents that produce 2-aryl-1,3-diketones, α-aryl-β-ketoesters, α-arylmalonate esters, α-aryl cyanoacetates, and α-aryl malononitriles, see refs 12a, e, f, o, p, and (a) Lindley, J. Tetrahedron 1984, 40, 1433 and references therein. In addition, α-aryl acetates: (b) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6855, α-aryl malonate esters: (c) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507. (d) Setsune, J.-I.; Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367. α-aryl cyanoacetates: (e) Suzuki, H.; Kobayashi, T.; Yoshida, Y.; Osuka, A. Chem. Lett. 1983, 193. α-aryl malononitriles: (f) Suzuki, H.; Kobayashi, T.; Osuka, A. Chem. Lett. 1983, 589. α-aryl phenylsulfonyl- acetonitriles: (g) Suzuki, H.; Yi, Q.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887.
45. For reagents that produce 2-aryl-1,3-diketones, α-aryl-β-ketoesters, α-arylmalonate esters, α-aryl cyanoacetates, and α-aryl malononitriles, see refs 12a, e, f, o, p, and (a) Lindley, J. Tetrahedron 1984, 40, 1433 and references therein. In addition, α-aryl acetates: (b) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6855, α-aryl malonate esters: (c) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507. (d) Setsune, J.-I.; Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367. α-aryl cyanoacetates: (e) Suzuki, H.; Kobayashi, T.; Yoshida, Y.; Osuka, A. Chem. Lett. 1983, 193. α-aryl malononitriles: (f) Suzuki, H.; Kobayashi, T.; Osuka, A. Chem. Lett. 1983, 589. α-aryl phenylsulfonyl- acetonitriles: (g) Suzuki, H.; Yi, Q.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887.
46. For reagents that produce 2-aryl-1,3-diketones, α-aryl-β-ketoesters, α-arylmalonate esters, α-aryl cyanoacetates, and α-aryl malononitriles, see refs 12a, e, f, o, p, and (a) Lindley, J. Tetrahedron 1984, 40, 1433 and references therein. In addition, α-aryl acetates: (b) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6855, α-aryl malonate esters: (c) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507. (d) Setsune, J.-I.; Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367. α-aryl cyanoacetates: (e) Suzuki, H.; Kobayashi, T.; Yoshida, Y.; Osuka, A. Chem. Lett. 1983, 193. α-aryl malononitriles: (f) Suzuki, H.; Kobayashi, T.; Osuka, A. Chem. Lett. 1983, 589. α-aryl phenylsulfonyl- acetonitriles: (g) Suzuki, H.; Yi, Q.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887.
47. For reagents that produce 2-aryl-1,3-diketones, α-aryl-β-ketoesters, α-arylmalonate esters, α-aryl cyanoacetates, and α-aryl malononitriles, see refs 12a, e, f, o, p, and (a) Lindley, J. Tetrahedron 1984, 40, 1433 and references therein. In addition, α-aryl acetates: (b) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6855, α-aryl malonate esters: (c) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507. (d) Setsune, J.-I.; Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367. α-aryl cyanoacetates: (e) Suzuki, H.; Kobayashi, T.; Yoshida, Y.; Osuka, A. Chem. Lett. 1983, 193. α-aryl malononitriles: (f) Suzuki, H.; Kobayashi, T.; Osuka, A. Chem. Lett. 1983, 589. α-aryl phenylsulfonyl- acetonitriles: (g) Suzuki, H.; Yi, Q.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887.
48. For reagents that produce 2-aryl-1,3-diketones, α-aryl-β-ketoesters, α-arylmalonate esters, α-aryl cyanoacetates, and α-aryl malononitriles, see refs 12a, e, f, o, p, and (a) Lindley, J. Tetrahedron 1984, 40, 1433 and references therein. In addition, α-aryl acetates: (b) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6855, α-aryl malonate esters: (c) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507. (d) Setsune, J.-I.; Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367. α-aryl cyanoacetates: (e) Suzuki, H.; Kobayashi, T.; Yoshida, Y.; Osuka, A. Chem. Lett. 1983, 193. α-aryl malononitriles: (f) Suzuki, H.; Kobayashi, T.; Osuka, A. Chem. Lett. 1983, 589. α-aryl phenylsulfonyl- acetonitriles: (g) Suzuki, H.; Yi, Q.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887.
49. For reagents that produce 2-aryl-1,3-diketones, α-aryl-β-ketoesters, α-arylmalonate esters, α-aryl cyanoacetates, and α-aryl malononitriles, see refs 12a, e, f, o, p, and (a) Lindley, J. Tetrahedron 1984, 40, 1433 and references therein. In addition, α-aryl acetates: (b) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6855, α-aryl malonate esters: (c) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507. (d) Setsune, J.-I.; Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367. α-aryl cyanoacetates: (e) Suzuki, H.; Kobayashi, T.; Yoshida, Y.; Osuka, A. Chem. Lett. 1983, 193. α-aryl malononitriles: (f) Suzuki, H.; Kobayashi, T.; Osuka, A. Chem. Lett. 1983, 589. α-aryl phenylsulfonyl-acetonitriles: (g) Suzuki, H.; Yi, Q.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887.
50. For reagents that produce 2-aryl-1,3-diketones, α-aryl-β-ketoesters, α-arylmalonate esters, α-aryl cyanoacetates, and α-aryl malononitriles, see refs 12a, e, f, o, p, and (a) Lindley, J. Tetrahedron 1984, 40, 1433 and references therein. In addition, α-aryl acetates: (b) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6855, α-aryl malonate esters: (c) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507. (d) Setsune, J.-I.; Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367. α-aryl cyanoacetates: (e) Suzuki, H.; Kobayashi, T.; Yoshida, Y.; Osuka, A. Chem. Lett. 1983, 193. α-aryl malononitriles: (f) Suzuki, H.; Kobayashi, T.; Osuka, A. Chem. Lett. 1983, 589. α-aryl phenylsulfonyl- acetonitriles: (g) Suzuki, H.; Yi, Q.; Inoue, J.; Kusume, K.; Ogawa, T. Chem. Lett. 1987, 887.
51. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
52. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
53. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
54. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
55. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
56. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
57. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
58. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni-catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
59. 3SnF or CuF: (h) Agnelli, F.; Sulikowski, G. A. Tetrahedon Lett. 1998, 39, 8807. Ni- catalyzed coupling of aryl-Grignard reagents with α-bromopropionate esters: (i) Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Manzo, S.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
60. 3SnF: (a) Kuwajima, I.;
61. 3SnOMe: (b) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn. 1984, 57, 242. Ni-catalyzed arylations of α-bromosilyl enol ethers: (c) Tamao, K.; Zembayashi, M.; Kumada, M. Chem. Lett. 1976, 1239. Ni-catalyzed electrochemical couplings of aryl halides with α-halo ketones and α-halo esters: (d) Durandetti, M.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748 and references therein.
62. 3SnOMe: (b) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn. 1984, 57, 242. Ni-catalyzed arylations of α-bromosilyl enol ethers: (c) Tamao, K.; Zembayashi, M.; Kumada, M. Chem. Lett. 1976, 1239. Ni-catalyzed electrochemical couplings of aryl halides with α-halo ketones and α-halo esters: (d) Durandetti, M.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748 and references therein.
63. 3SnOMe: (b) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn. 1984, 57, 242. Ni-catalyzed arylations of α-bromosilyl enol ethers: (c) Tamao, K.; Zembayashi, M.; Kumada, M. Chem. Lett. 1976, 1239. Ni-catalyzed electrochemical couplings of aryl halides with α-halo ketones and α-halo esters: (d) Durandetti, M.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748 and references therein.
64. Ni-catalyzed coupling of a lithium ester enolate: (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Cu-catalyzed arylation of β-dicarbonyl compounds with 2-bromobenzoic acids: (b) Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607 and references therein. Cu- catalyzed reaction of aryliodides with ethyl cyanoacetate, malononitrile, or acetylacetone: (c) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 7606. Pd-catalyzed reactions of aryl bromides or aryl iodides with alkyl cyanoacetates or malononitrile: (d) Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932. (e) Sakamoto, T.; Katoh, E.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1664 and references therein.
65. Ni-catalyzed coupling of a lithium ester enolate: (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Cu-catalyzed arylation of β-dicarbonyl compounds with 2-bromobenzoic acids: (b) Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607 and references therein. Cu-catalyzed reaction of aryliodides with ethyl cyanoacetate, malononitrile, or acetylacetone: (c) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 7606. Pd-catalyzed reactions of aryl bromides or aryl iodides with alkyl cyanoacetates or malononitrile: (d) Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932. (e) Sakamoto, T.; Katoh, E.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1664 and references therein.
66. Ni-catalyzed coupling of a lithium ester enolate: (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Cu-catalyzed arylation of β-dicarbonyl compounds with 2-bromobenzoic acids: (b) Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607 and references therein. Cu- catalyzed reaction of aryliodides with ethyl cyanoacetate, malononitrile, or acetylacetone: (c) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 7606. Pd-catalyzed reactions of aryl bromides or aryl iodides with alkyl cyanoacetates or malononitrile: (d) Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932. (e) Sakamoto, T.; Katoh, E.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1664 and references therein.
67. Ni-catalyzed coupling of a lithium ester enolate: (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Cu-catalyzed arylation of β-dicarbonyl compounds with 2-bromobenzoic acids: (b) Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607 and references therein. Cu- catalyzed reaction of aryliodides with ethyl cyanoacetate, malononitrile, or acetylacetone: (c) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 7606. Pd-catalyzed reactions of aryl bromides or aryl iodides with alkyl cyanoacetates or malononitrile: (d) Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932. (e) Sakamoto, T.; Katoh, E.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1664 and references therein.
68. Ni-catalyzed coupling of a lithium ester enolate: (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Cu-catalyzed arylation of β-dicarbonyl compounds with 2-bromobenzoic acids: (b) Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607 and references therein. Cu- catalyzed reaction of aryliodides with ethyl cyanoacetate, malononitrile, or acetylacetone: (c) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 7606. Pd-catalyzed reactions of aryl bromides or aryl iodides with alkyl cyanoacetates or malononitrile: (d) Uno, M.; Seto, K.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1984, 932. (e) Sakamoto, T.; Katoh, E.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1664 and references therein.
69. For catalytic, intramolecular arylations of ketones and 1,3-diketones, see ref 13c and (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (c) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. For a catalytic intramolecular vinylation of a ketone, see: (d) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11.
70. For catalytic, intramolecular arylations of ketones and 1,3-diketones, see ref 13c and (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (c) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. For a catalytic intramolecular vinylation of a ketone, see: (d) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11.
71. For catalytic, intramolecular arylations of ketones and 1,3-diketones, see ref 13c and (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (c) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. For a catalytic intramolecular vinylation of a ketone, see: (d) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11.
72. For catalytic, intramolecular arylations of ketones and 1,3-diketones, see ref 13c and (a) Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4151. (b) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7577. (c) Muratake, H.; Hayakawa, A.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581. For a catalytic intramolecular vinylation of a ketone, see: (d) Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11.
73. Hou, D.; Mas, J. L. U.S. Patent 4,992,591, 1991; Chem. Abstr. 1991, 115, 28927z.
74. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
75. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
76. (a) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
77. (b) Satoh, T.; Inoh, J.-I.; Kawamura, Y.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 2239.
78. (a) Palucki, M. P.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.
79. (b) Palucki, M. P.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 19, 3395.
80. DBA = dibenzylidene acetone. Tol-BINAP = 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl. BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.
81. Related work by Miura and co-workers: (a) Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 1998, 39, 6203.
82. (b) Satoh, T.; Kametani, Y.; Terao, Y.; Miura, M.; Nomura, M. Tetrahedron Lett. 1999, 40, 5345.
83. Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 63, 6546.
84. Wang, D.; Wu, Z. J. Chem. Soc., Chem. Commun. 1999, 529.
85. Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918.
86. (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
87. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
88. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
89. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
90. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
91. Ligands 4 and 5 are commercially available from Strem Chemical Co.
92. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
93. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
94. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem., in press.
95. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
96. Xantphos = 9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene. For its preparation, see: (a) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics, 1995, 14, 3081. For the use of Xantphos in Pd-catalyzed amination reactions, see: (b) Guari, Y.; van Es, D. S.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Lett. 1999, 40, 3789. For the use of Xantphos in the Pd-catalyzed preparation of N-aryl benzophenone hydrazones, and subsequent conversion to indoles, see: (c) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
97. Xantphos = 9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene. For its preparation, see: (a) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics, 1995, 14, 3081. For the use of Xantphos in Pd-catalyzed amination reactions, see: (b) Guari, Y.; van Es, D. S.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Lett. 1999, 40, 3789. For the use of Xantphos in the Pd-catalyzed preparation of N-aryl benzophenone hydrazones, and subsequent conversion to indoles, see: (c) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
98. Xantphos = 9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene. For its preparation, see: (a) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics, 1995, 14, 3081. For the use of Xantphos in Pd-catalyzed amination reactions, see: (b) Guari, Y.; van Es, D. S.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Lett. 1999, 40, 3789. For the use of Xantphos in the Pd-catalyzed preparation of N-aryl benzophenone hydrazones, and subsequent conversion to indoles, see: (c) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
99. For the Cu-catalyzed, intermolecular reaction of acetylacetone with iodobenzene, see ref 16c. For Cu-catalyzed reactions of 1,3-diketones with o-bromobenzoic acid or related derivatives, see refs 13a and 16b.
100. Intramolecular arylations of nitroalkanes have been described: (a) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. For Pd-catalyzed arylations of 4-alkyl nitrobenzenes, see: (b) Inoh, J. I.; Satoh, T.; Pivsa- Art, S.; Miura, M.; Nomura, M. Tetrahedron Lett. 1998, 39, 4673.
101. Intramolecular arylations of nitroalkanes have been described: (a) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355. For Pd-catalyzed arylations of 4-alkyl nitrobenzenes, see: (b) Inoh, J. I.; Satoh, T.; Pivsa-Art, S.; Miura, M.; Nomura, M. Tetrahedron Lett. 1998, 39, 4673.
102. 4, see: Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619.
103. 1-acac) are stable as solids or in solution at room temperature. See (a) Tanaka, H.; Isobe, K.; Kawaguchi, S.; Okeya, S. Bull. Chem. Soc. Jpn. 1984, 57, 1850 and references therein.
104. (a) Beller, M.; Fischer, H.; Hermann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
105. (b) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. J. Chem. Soc., Chem. Commun. 1998, 2095.
106. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
107. Kočovský, P.; Vyskočil, Š.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714.
108. 2Pd(Ph)(Cl), the substitution of the phosphines is trans. See: Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1989, 28, 1386.
109. In palladium aryl halide and palladium aryl alkoxide complexes with BINAP, the ligand is chelating. See: Widenhofer, R. A.; Zhong, H. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787.
110. For crystal structures of Xantphos/Pd complexes, see: Kranenburg, M.; Delis, J. G. P.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Veldman, N.; Spek, A. L.; Goubitz, K.; Fraanje, J. J. Chem. Soc., Dalton Trans. 1997, 11, 1839.
111. Tossidis, I. Inorg. Nucl. Chem. Lett. 1976, 12, 609.
112. Bell, R. P.; Smith, P. W. J. Chem. Soc. (B) 1966, 241.
113. Ethanolic sodium ethoxide is known to convert diethyl α-phenyl-malonate to ethyl phenylacetate. See: Connor, R. J. Am. Chem. Soc. 1933, 55, 4597.
114. NaHMDS can also be purchased in either THF or toluene solution from Aldrich Chemical Co. These solutions can be handled without using a glovebox.
115. Tomori, H.; Buchwald, S. L., unpublished results.