Alkynylzirconation of alkynes and application to one-pot bisalkynylation of alkynes

Journal of Organic Chemistry

Volumn 67, Issue 21, 2002, Pages 7451-7456

  Liu, Yuanhong ^a   Zhong, Zhenqi ^a   Nakajima, Kiyohiko ^a,b   Takahashi, Tamotsu ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b AICHI UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BISALKYNYLATION;

DERIVATIVES; HYDROLYSIS;

ALCOHOLS;

ALKYNE DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; STEREOCHEMISTRY;

EID: 0037131239     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026037e     Document Type: Article

References (54)

1. For reviews on carbometalation of alkynes, see (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 865-911. (b) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870. (d) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wileyvch, Weinheim, Germany, 1998; pp 271-337. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
2. For reviews on carbometalation of alkynes, see (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 865-911. (b) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870. (d) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wileyvch, Weinheim, Germany, 1998; pp 271-337. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
3. For reviews on carbometalation of alkynes, see (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 865-911. (b) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870. (d) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wileyvch, Weinheim, Germany, 1998; pp 271-337. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
4. For reviews on carbometalation of alkynes, see (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 865-911. (b) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870. (d) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wileyvch, Weinheim, Germany, 1998; pp 271-337. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
5. For reviews on carbometalation of alkynes, see (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 865-911. (b) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870. (d) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wileyvch, Weinheim, Germany, 1998; pp 271-337. (e) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
6. For acyl-metalation of alkynes, see: (a) Hoberg, H.; Schaefer, D.; Burkhart, G.; Krüger, C.; Romao, M. J. J. Organomet. Chem. 1984, 266, 203 and references therein. (b) Hoberg, H.; Apotecher, B. J. Organomet. Chem. 1984, 270, C15. (c) DeShong, P.; Sidler, D. R.; Rybczynski, P. J.; Slough, G. A.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 2575. (d) DeShong, P.; Sidler, D. R. J. Org. Chem. 1988, 53, 4892. (e) Takai, K.; Kataoka, Y.; Yoshizumi, K.; Oguchi, Y.; Utimoto, K. Chem. Lett. 1991, 1479-1482.
7. For acyl-metalation of alkynes, see: (a) Hoberg, H.; Schaefer, D.; Burkhart, G.; Krüger, C.; Romao, M. J. J. Organomet. Chem. 1984, 266, 203 and references therein. (b) Hoberg, H.; Apotecher, B. J. Organomet. Chem. 1984, 270, C15. (c) DeShong, P.; Sidler, D. R.; Rybczynski, P. J.; Slough, G. A.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 2575. (d) DeShong, P.; Sidler, D. R. J. Org. Chem. 1988, 53, 4892. (e) Takai, K.; Kataoka, Y.; Yoshizumi, K.; Oguchi, Y.; Utimoto, K. Chem. Lett. 1991, 1479-1482.
8. For acyl-metalation of alkynes, see: (a) Hoberg, H.; Schaefer, D.; Burkhart, G.; Krüger, C.; Romao, M. J. J. Organomet. Chem. 1984, 266, 203 and references therein. (b) Hoberg, H.; Apotecher, B. J. Organomet. Chem. 1984, 270, C15. (c) DeShong, P.; Sidler, D. R.; Rybczynski, P. J.; Slough, G. A.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 2575. (d) DeShong, P.; Sidler, D. R. J. Org. Chem. 1988, 53, 4892. (e) Takai, K.; Kataoka, Y.; Yoshizumi, K.; Oguchi, Y.; Utimoto, K. Chem. Lett. 1991, 1479-1482.
9. For acyl-metalation of alkynes, see: (a) Hoberg, H.; Schaefer, D.; Burkhart, G.; Krüger, C.; Romao, M. J. J. Organomet. Chem. 1984, 266, 203 and references therein. (b) Hoberg, H.; Apotecher, B. J. Organomet. Chem. 1984, 270, C15. (c) DeShong, P.; Sidler, D. R.; Rybczynski, P. J.; Slough, G. A.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 2575. (d) DeShong, P.; Sidler, D. R. J. Org. Chem. 1988, 53, 4892. (e) Takai, K.; Kataoka, Y.; Yoshizumi, K.; Oguchi, Y.; Utimoto, K. Chem. Lett. 1991, 1479-1482.
10. For acyl-metalation of alkynes, see: (a) Hoberg, H.; Schaefer, D.; Burkhart, G.; Krüger, C.; Romao, M. J. J. Organomet. Chem. 1984, 266, 203 and references therein. (b) Hoberg, H.; Apotecher, B. J. Organomet. Chem. 1984, 270, C15. (c) DeShong, P.; Sidler, D. R.; Rybczynski, P. J.; Slough, G. A.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 2575. (d) DeShong, P.; Sidler, D. R. J. Org. Chem. 1988, 53, 4892. (e) Takai, K.; Kataoka, Y.; Yoshizumi, K.; Oguchi, Y.; Utimoto, K. Chem. Lett. 1991, 1479-1482.
11. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
12. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
13. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
14. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
15. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
16. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
17. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
18. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
19. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
20. For alkenyl-metalation of alkynes, see the following. For Cu: (a) Negishi, E. Acc. Chem. Res. 1987, 20, 65-72. (b) Normant, J. F.; Cahiez, G.; Bourgain, M.; Chuit, C.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 1656-1666. (c) Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1982, 23, 5151-5154. (d) Furber, M.; Taylor, R. J. K.; Burford, S. C. Tetrahedron Lett. 1985, 26, 3285-3288. (e) Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815. For Al: (f) Wilke, G.; Muller, H. Chem. Ber. 1956, 89, 444-447. (g) Eisch, J. J.; Kaska. W. C. J. Am. Chem. Soc. 1966, 88, 2213-2220. (h) Zweifel, G.; Snow, J. T.; Whitney, C. C. J. Am. Chem. Soc. 1968, 90, 7139-7141. For Mg: (i) Richey, H. G., Jr.; Von Rein, F. W. J. Organomet. Chem. 1969, 20, P32-35. For Zr: (j) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871-5872.
21. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
22. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
23. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
24. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
25. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
26. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
27. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
28. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
29. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
30. For allyl-metalation of alkynes, see the following. For Mg: (a) Richey, H. G.; Von Rein, F. W. Tetrahedron Lett. 1971, 3777. (b) Eisch, J. J.; Merkley, J. H.; Galle, J. E. J. Org. Chem. 1979, 44, 587. For Zn: (c) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (d) Bernardou, F.; Miginiac, L. J. Organomet. Chem. 1977, 125, 23. (e) Negishi, E.; Miller, J. A. J. Am. Chem. Soc., 1983, 105, 6761-6763. For Al: (f) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. For Zr: (g) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519-4540. (h) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685. (i) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031-3034. For Sn: (j) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222.
31. Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228-3229.
32. Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976.
33. Horton, A. D. J. Chem. Soc., Chem. Commun. 1992, 185-187.
34. (a) Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 1503-1504.
35. (b) Takahashi, T.; Xi, Z.; Kotora, M.; Xi, C.; Nakajima, K. Tetrahedron Lett. 1996, 37, 7521-7524.
36. (c) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154-5155.
37. (d) Hara, R.; NIshihara, Y.; Landre, P. D.; Takahashi, T. Tetrahedron Lett. 1997, 38, 447-450.
38. Takahashi, T.; Suzuki, N.; Kageyama, M.; Nitto, Y.; Saburi, M.; Negishi, E. Chem. Lett. 1991, 1579-1582.
39. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867.
40. Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091.
41. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.
42. (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol 3, pp 521-549.
43. Petasis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805.
44. Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107-2108.
45. Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1992, 114, 5859-5860.
46. (a) Yoshimatsu, M.; Yamada, H.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Chem. Commun. 1994, 2107-2108.
47. (b) Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Grierson, D. S. Synlett 1993, 20-22.
48. (c) Shibuya, M.; Sakai, Y.; Naoe, Y. Tetrahedron Lett. 1995, 36, 897-898.
49. (d) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1995, 117, 8875-8876.
50. It has been reported that enediynes undergo cis-trans isomerization under heating or irradiation. (a) Vollhardt, K. P. C.; Winn. L. S. Tetrahedron Lett. 1985, 26, 709-712. (b) König, B.; Schofield, E.; Bubenitschek, P.; Jones, P. G. J. Org. Chem. 1994, 59, 7142-7143. (c) Martin, R. E.; Bartek, J.; Diederich, F.; Tykwinski, R. R.; Meister, E. C.; Hilger, A.; Lüthi, H. P. J. Chem. Soc., Perkin Trans. 1998, 233. (d) Shimizu, T.; Miyasaka, D.; Kamigata, N. Org. Lett. 2000, 2, 1923-1925. (e) Diederich, F. Chem. Commun. 2001, 219-227.
51. It has been reported that enediynes undergo cis-trans isomerization under heating or irradiation. (a) Vollhardt, K. P. C.; Winn. L. S. Tetrahedron Lett. 1985, 26, 709-712. (b) König, B.; Schofield, E.; Bubenitschek, P.; Jones, P. G. J. Org. Chem. 1994, 59, 7142-7143. (c) Martin, R. E.; Bartek, J.; Diederich, F.; Tykwinski, R. R.; Meister, E. C.; Hilger, A.; Lüthi, H. P. J. Chem. Soc., Perkin Trans. 1998, 233. (d) Shimizu, T.; Miyasaka, D.; Kamigata, N. Org. Lett. 2000, 2, 1923-1925. (e) Diederich, F. Chem. Commun. 2001, 219-227.
52. It has been reported that enediynes undergo cis-trans isomerization under heating or irradiation. (a) Vollhardt, K. P. C.; Winn. L. S. Tetrahedron Lett. 1985, 26, 709-712. (b) König, B.; Schofield, E.; Bubenitschek, P.; Jones, P. G. J. Org. Chem. 1994, 59, 7142-7143. (c) Martin, R. E.; Bartek, J.; Diederich, F.; Tykwinski, R. R.; Meister, E. C.; Hilger, A.; Lüthi, H. P. J. Chem. Soc., Perkin Trans. 1998, 233. (d) Shimizu, T.; Miyasaka, D.; Kamigata, N. Org. Lett. 2000, 2, 1923-1925. (e) Diederich, F. Chem. Commun. 2001, 219-227.
53. It has been reported that enediynes undergo cis-trans isomerization under heating or irradiation. (a) Vollhardt, K. P. C.; Winn. L. S. Tetrahedron Lett. 1985, 26, 709-712. (b) König, B.; Schofield, E.; Bubenitschek, P.; Jones, P. G. J. Org. Chem. 1994, 59, 7142-7143. (c) Martin, R. E.; Bartek, J.; Diederich, F.; Tykwinski, R. R.; Meister, E. C.; Hilger, A.; Lüthi, H. P. J. Chem. Soc., Perkin Trans. 1998, 233. (d) Shimizu, T.; Miyasaka, D.; Kamigata, N. Org. Lett. 2000, 2, 1923-1925. (e) Diederich, F. Chem. Commun. 2001, 219-227.
54. It has been reported that enediynes undergo cis-trans isomerization under heating or irradiation. (a) Vollhardt, K. P. C.; Winn. L. S. Tetrahedron Lett. 1985, 26, 709-712. (b) König, B.; Schofield, E.; Bubenitschek, P.; Jones, P. G. J. Org. Chem. 1994, 59, 7142-7143. (c) Martin, R. E.; Bartek, J.; Diederich, F.; Tykwinski, R. R.; Meister, E. C.; Hilger, A.; Lüthi, H. P. J. Chem. Soc., Perkin Trans. 1998, 233. (d) Shimizu, T.; Miyasaka, D.; Kamigata, N. Org. Lett. 2000, 2, 1923-1925. (e) Diederich, F. Chem. Commun. 2001, 219-227.