Copper-mediated coupling of zirconacyclopentadienes with dihalo aromatic compounds. Formation of fused aromatic rings

Journal of the American Chemical Society

Volumn 118, Issue 21, 1996, Pages 5154-5155

  Takahashi, Tamotsu ^a   Hara, Ryuichiro ^a   Nishihara, Yasushi ^a   Kotora, Martin ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; COPPER COMPOUNDS; MOLECULAR STRUCTURE; ORGANOMETALLICS; SYNTHESIS (CHEMICAL);

COUPLINGS; DIHALO AROMATIC COMPOUNDS; FUSED AROMATIC RINGS; ZIRCONACYCLOPENTADIENES;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; COPPER; UNCLASSIFIED DRUG; ZIRCONACYCLOPENTADIENE;

ARTICLE; CHEMICAL REACTION; DRUG HYDROLYSIS; DRUG SYNTHESIS;

EID: 15844405617     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960407x     Document Type: Article

References (36)

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4. For symmetrical zirconacyclopentadienes, see: (a) Braye, E. H.; Hubel, W.; Capelier, I. J. Am. Chem. Soc. 1961, 83, 4406-4413. (b) Sonogashira, K.; Hagihara, N. Bull. Chem. Soc. Jpn. 1966, 39, 1178-1182. (c) Watt, G. W.; Drummond, F. O., Jr. J. Am. Chem. Soc. 1970, 92, 826-828. (d) Alt, H.; Rausch, M. D. J. Am. Chem. Soc. 1974, 96, 5936-5937. (e) Yoshifuji, M.; Gell, K. I.; Schwartz, J. J. Organomet. Chem. 1978, 153, C15-C18. (f) Hunter, W. E.; Atwood, J. L.; Fachinetti, G.; Floriani, C. J. Organomet. Chem. 1981, 204, 67-74. (g) Thanedar, S.; Farona, M. F. J. Organomet. Chem. 1982, 235, 65-68. (h) Skibbe, V.; Erker, G. J. Organomet. Chem. 1983, 241, 15-26.
5. For symmetrical zirconacyclopentadienes, see: (a) Braye, E. H.; Hubel, W.; Capelier, I. J. Am. Chem. Soc. 1961, 83, 4406-4413. (b) Sonogashira, K.; Hagihara, N. Bull. Chem. Soc. Jpn. 1966, 39, 1178-1182. (c) Watt, G. W.; Drummond, F. O., Jr. J. Am. Chem. Soc. 1970, 92, 826-828. (d) Alt, H.; Rausch, M. D. J. Am. Chem. Soc. 1974, 96, 5936-5937. (e) Yoshifuji, M.; Gell, K. I.; Schwartz, J. J. Organomet. Chem. 1978, 153, C15-C18. (f) Hunter, W. E.; Atwood, J. L.; Fachinetti, G.; Floriani, C. J. Organomet. Chem. 1981, 204, 67-74. (g) Thanedar, S.; Farona, M. F. J. Organomet. Chem. 1982, 235, 65-68. (h) Skibbe, V.; Erker, G. J. Organomet. Chem. 1983, 241, 15-26.
6. For symmetrical zirconacyclopentadienes, see: (a) Braye, E. H.; Hubel, W.; Capelier, I. J. Am. Chem. Soc. 1961, 83, 4406-4413. (b) Sonogashira, K.; Hagihara, N. Bull. Chem. Soc. Jpn. 1966, 39, 1178-1182. (c) Watt, G. W.; Drummond, F. O., Jr. J. Am. Chem. Soc. 1970, 92, 826-828. (d) Alt, H.; Rausch, M. D. J. Am. Chem. Soc. 1974, 96, 5936-5937. (e) Yoshifuji, M.; Gell, K. I.; Schwartz, J. J. Organomet. Chem. 1978, 153, C15-C18. (f) Hunter, W. E.; Atwood, J. L.; Fachinetti, G.; Floriani, C. J. Organomet. Chem. 1981, 204, 67-74. (g) Thanedar, S.; Farona, M. F. J. Organomet. Chem. 1982, 235, 65-68. (h) Skibbe, V.; Erker, G. J. Organomet. Chem. 1983, 241, 15-26.
7. For symmetrical zirconacyclopentadienes, see: (a) Braye, E. H.; Hubel, W.; Capelier, I. J. Am. Chem. Soc. 1961, 83, 4406-4413. (b) Sonogashira, K.; Hagihara, N. Bull. Chem. Soc. Jpn. 1966, 39, 1178-1182. (c) Watt, G. W.; Drummond, F. O., Jr. J. Am. Chem. Soc. 1970, 92, 826-828. (d) Alt, H.; Rausch, M. D. J. Am. Chem. Soc. 1974, 96, 5936-5937. (e) Yoshifuji, M.; Gell, K. I.; Schwartz, J. J. Organomet. Chem. 1978, 153, C15-C18. (f) Hunter, W. E.; Atwood, J. L.; Fachinetti, G.; Floriani, C. J. Organomet. Chem. 1981, 204, 67-74. (g) Thanedar, S.; Farona, M. F. J. Organomet. Chem. 1982, 235, 65-68. (h) Skibbe, V.; Erker, G. J. Organomet. Chem. 1983, 241, 15-26.
8. For symmetrical zirconacyclopentadienes, see: (a) Braye, E. H.; Hubel, W.; Capelier, I. J. Am. Chem. Soc. 1961, 83, 4406-4413. (b) Sonogashira, K.; Hagihara, N. Bull. Chem. Soc. Jpn. 1966, 39, 1178-1182. (c) Watt, G. W.; Drummond, F. O., Jr. J. Am. Chem. Soc. 1970, 92, 826-828. (d) Alt, H.; Rausch, M. D. J. Am. Chem. Soc. 1974, 96, 5936-5937. (e) Yoshifuji, M.; Gell, K. I.; Schwartz, J. J. Organomet. Chem. 1978, 153, C15-C18. (f) Hunter, W. E.; Atwood, J. L.; Fachinetti, G.; Floriani, C. J. Organomet. Chem. 1981, 204, 67-74. (g) Thanedar, S.; Farona, M. F. J. Organomet. Chem. 1982, 235, 65-68. (h) Skibbe, V.; Erker, G. J. Organomet. Chem. 1983, 241, 15-26.
9. For symmetrical zirconacyclopentadienes, see: (a) Braye, E. H.; Hubel, W.; Capelier, I. J. Am. Chem. Soc. 1961, 83, 4406-4413. (b) Sonogashira, K.; Hagihara, N. Bull. Chem. Soc. Jpn. 1966, 39, 1178-1182. (c) Watt, G. W.; Drummond, F. O., Jr. J. Am. Chem. Soc. 1970, 92, 826-828. (d) Alt, H.; Rausch, M. D. J. Am. Chem. Soc. 1974, 96, 5936-5937. (e) Yoshifuji, M.; Gell, K. I.; Schwartz, J. J. Organomet. Chem. 1978, 153, C15-C18. (f) Hunter, W. E.; Atwood, J. L.; Fachinetti, G.; Floriani, C. J. Organomet. Chem. 1981, 204, 67-74. (g) Thanedar, S.; Farona, M. F. J. Organomet. Chem. 1982, 235, 65-68. (h) Skibbe, V.; Erker, G. J. Organomet. Chem. 1983, 241, 15-26.
10. For symmetrical zirconacyclopentadienes, see: (a) Braye, E. H.; Hubel, W.; Capelier, I. J. Am. Chem. Soc. 1961, 83, 4406-4413. (b) Sonogashira, K.; Hagihara, N. Bull. Chem. Soc. Jpn. 1966, 39, 1178-1182. (c) Watt, G. W.; Drummond, F. O., Jr. J. Am. Chem. Soc. 1970, 92, 826-828. (d) Alt, H.; Rausch, M. D. J. Am. Chem. Soc. 1974, 96, 5936-5937. (e) Yoshifuji, M.; Gell, K. I.; Schwartz, J. J. Organomet. Chem. 1978, 153, C15-C18. (f) Hunter, W. E.; Atwood, J. L.; Fachinetti, G.; Floriani, C. J. Organomet. Chem. 1981, 204, 67-74. (g) Thanedar, S.; Farona, M. F. J. Organomet. Chem. 1982, 235, 65-68. (h) Skibbe, V.; Erker, G. J. Organomet. Chem. 1983, 241, 15-26.
11. For zirconacyclopentadienes prepared from diynes, see: (a) Negishi, E.; Swanson, D. R.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829-2832. (b) Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788-2796. (c) Negishi, E.; Holms, S. J.; Tour, J.; Miller, J. A.; Cederbaum, F. .E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336-3346.
12. For zirconacyclopentadienes prepared from diynes, see: (a) Negishi, E.; Swanson, D. R.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829-2832. (b) Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788-2796. (c) Negishi, E.; Holms, S. J.; Tour, J.; Miller, J. A.; Cederbaum, F. .E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336-3346.
13. For zirconacyclopentadienes prepared from diynes, see: (a) Negishi, E.; Swanson, D. R.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829-2832. (b) Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788-2796. (c) Negishi, E.; Holms, S. J.; Tour, J.; Miller, J. A.; Cederbaum, F. .E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336-3346.
14. For unsymmetrical zirconacyclopentadienes, see: (a) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (b) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546. (c) Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874. (d) Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. (e) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690. (f) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448.
15. For unsymmetrical zirconacyclopentadienes, see: (a) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (b) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546. (c) Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874. (d) Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. (e) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690. (f) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448.
16. For unsymmetrical zirconacyclopentadienes, see: (a) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (b) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546. (c) Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874. (d) Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. (e) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690. (f) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448.
17. For unsymmetrical zirconacyclopentadienes, see: (a) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (b) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546. (c) Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874. (d) Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. (e) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690. (f) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448.
18. For unsymmetrical zirconacyclopentadienes, see: (a) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (b) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546. (c) Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874. (d) Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. (e) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690. (f) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448.
19. For unsymmetrical zirconacyclopentadienes, see: (a) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626. (b) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544-2546. (c) Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870-2874. (d) Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498. (e) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690. (f) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448.
20. 2 with an excess of diphenylacetylene gave cyclopentadienone as a minor product. See: (b) Sikora, D. J.; Rausch, M. P. J. Organomet. Chem. 1984, 276, 21-37. For main group heterocycle formation from zirconacyclopentadienes, see: (c) Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310-2312. (d) Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880-1889.
21. 2 with an excess of diphenylacetylene gave cyclopentadienone as a minor product. See: (b) Sikora, D. J.; Rausch, M. P. J. Organomet. Chem. 1984, 276, 21-37. For main group heterocycle formation from zirconacyclopentadienes, see: (c) Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310-2312. (d) Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880-1889.
22. 2 with an excess of diphenylacetylene gave cyclopentadienone as a minor product. See: (b) Sikora, D. J.; Rausch, M. P. J. Organomet. Chem. 1984, 276, 21-37. For main group heterocycle formation from zirconacyclopentadienes, see: (c) Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310-2312. (d) Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880-1889.
23. 2 with an excess of diphenylacetylene gave cyclopentadienone as a minor product. See: (b) Sikora, D. J.; Rausch, M. P. J. Organomet. Chem. 1984, 276, 21-37. For main group heterocycle formation from zirconacyclopentadienes, see: (c) Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310-2312. (d) Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880-1889.
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26. For transmetalation of other zirconacycles to Cu, see: (a) Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109-110. (b) Lipshutz, B. H.; Segi, M. Tetrahedron 1995, 51, 4407-4420.
27. For transmetalation of other zirconacycles to Cu, see: (a) Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109-110. (b) Lipshutz, B. H.; Segi, M. Tetrahedron 1995, 51, 4407-4420.
28. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
29. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
30. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
31. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
32. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
33. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
34. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
35. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
36. Transmetalation of alkenyl carbons from zirconium to copper has been reported. See: (a) Yoshifuji, M.; Loots, M.; Schwartz, J. Tetrahedron Lett. 1977, 1303-1306. (b) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440-7441. (c) Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLanghlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L. J. Am. Chem. Soc. 1990, 112, 7441-7442. (d) Lipshutz, B. H.; Hato, K. Tetrahedron Lett., 1991, 32, 5647-5650. (e) Lipshutz, B. H.; Fatheree, P.; Hagan, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041-1044. (f) Lipshutz, B. H.; Keil, R. J. Am. Chem. Soc. 1992, 114, 7919-7920. (g) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625-12626. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685-5688. (i) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.