α-trifluoromethyl-substituted β-ethoxyvinyl zinc reagent: Preparation and palladium-catalyzed cross-coupling as a novel route to functionalized CF3-containing compounds

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 3200-3204

  Shi, Guo Qiang ^a   Huang, Xian Hai ^a   Hong, Feng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001555347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952215a     Document Type: Article

References (36)

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3. (c) McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555.
4. (d) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood: Chichester, 1992.
5. For recent reviews see (a) Burton, D. J.; Yang, Z.-Y.; Morken, D. A. Tetrahedron 1994, 50, 2993. (b) Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189.
6. For recent reviews see (a) Burton, D. J.; Yang, Z.-Y.; Morken, D. A. Tetrahedron 1994, 50, 2993. (b) Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189.
7. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
8. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
9. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
10. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
11. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
12. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
13. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
14. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
15. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
16. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
17. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
18. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
19. 3-substituted organometallic reagents, see (a) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199. (b) Yamazaki, T.; Hiraoka, S.; Kitazame, T. J. Org. Chem. 1994, 59, 5100. (c) Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758. (d) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941. (e) Qian C.-P.; Nakai, T. Tetrahedron Lett. 1990, 31, 7043. (f) Kitagawa, O.; Hashimoto, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307. (g) Ishihara T.; Kuroboshi, M.; Yamaguchi, K. Chem. Lett. 1990, 211. (h) Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. (i) Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 3321. (j) Yokozawa, T.; Ishikawa, N.; Nakai, T. Chem. Lett. 1987, 1971. (k) Hemer, I.; Posta, A.; Dedek, V. J. Fluorine Chem. 1984, 61, 3321. (l) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276 and references cited therein. (m) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481. (n) Arakesmith, F. G.; Steward, O. J.; Tarrant, P. J. Org. Chem. 1968, 33, 280.
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