Rhodium-Catalyzed Coupling Reaction of Salicyl Aldehydes with Alkynes via Cleavage of the Aldehyde C-H Bond

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4564-4565

  Kokubo, Ken ^a   Matsumasa, Kenji ^a   Miura, Masahiro ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000099596     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9709458     Document Type: Article

References (42)

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2. For reviews, see: (a) Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451. (b) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
3. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
4. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
5. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
6. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
7. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
8. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
9. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
10. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
11. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
12. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
13. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
14. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
15. Satoh, T.; Itaya, T.; Miura, M.; Nomura, M. Chem. Lett. 1996, 823.
16. For example: (a) Coffey, S. Rodd's Chemistry of Carbon Compounds, 2nd Ed.; Elsevier: Amsterdam, 1977; Vol. IV, Part E. (b) Katritzky, A.; Rees, C. W. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., Mckillop, A., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 573-883.
17. For example: (a) Coffey, S. Rodd's Chemistry of Carbon Compounds, 2nd Ed.; Elsevier: Amsterdam, 1977; Vol. IV, Part E. (b) Katritzky, A.; Rees, C. W. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., Mckillop, A., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, pp 573-883.
18. (a) Kasahara, A.; Izumi, T.; Ooshima, M. Bull. Chem. Soc. Jpn. 1974, 47, 2526.
19. (b) Cullen, W. P.; Donnelly, D. M. X.; Keenan, A. K.; Keenan, P. J.; Ramdas, K. J. Chem. Soc., Perkin Trans. 1 1975, 1671.
20. Furlong, J. J. P.; Nudelman, N. S. J. Chem. Soc., Perkin Trans. 2 1988, 1213.
21. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
22. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
23. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
24. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
25. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
26. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
27. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
28. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
29. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
30. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
31. 7j8e has been little known: (a) Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190. Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. Okano, T.; Kobayashi, T.; Konishi, H.; Kiji, J. Tetrahedron Lett. 1982, 23, 4967. (e) Rode, E.; Davis, M. E.; Hanson, B. E. J. Chem. Soc., Chem. Commun. 1985, 716. (f) Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451. (g) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 946. (h) Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821. (j) Lee, H.; Jun, C.-H. Bull. Korean Chem. Soc. 1995, 16, 1135; Chem. Abstr. 1996, 124, 202420b.
32. Rh-catalyzed reaction of aldimines with alkenes: (a) Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489. (b) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200. Ru-catalyzed hydroacylation of alkenes: Isnard, P.; Denise, B.; Sneeden, R. P. A.; Congnion, J. M.; Durual, P. J. Organomet. Chem. 1982, 240, 285. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. Ni-catalyzed hydroacylation of alkynes: (e) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. Very recently, efficient Co-catalyzed hydroacylation of alkenes has also been reported: (f) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
33. Rh-catalyzed reaction of aldimines with alkenes: (a) Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489. (b) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200. Ru-catalyzed hydroacylation of alkenes: Isnard, P.; Denise, B.; Sneeden, R. P. A.; Congnion, J. M.; Durual, P. J. Organomet. Chem. 1982, 240, 285. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. Ni-catalyzed hydroacylation of alkynes: (e) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. Very recently, efficient Co-catalyzed hydroacylation of alkenes has also been reported: (f) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
34. Rh-catalyzed reaction of aldimines with alkenes: (a) Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489. (b) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200. Ru-catalyzed hydroacylation of alkenes: Isnard, P.; Denise, B.; Sneeden, R. P. A.; Congnion, J. M.; Durual, P. J. Organomet. Chem. 1982, 240, 285. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. Ni-catalyzed hydroacylation of alkynes: (e) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. Very recently, efficient Co-catalyzed hydroacylation of alkenes has also been reported: (f) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
35. Rh-catalyzed reaction of aldimines with alkenes: (a) Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489. (b) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200. Ru-catalyzed hydroacylation of alkenes: Isnard, P.; Denise, B.; Sneeden, R. P. A.; Congnion, J. M.; Durual, P. J. Organomet. Chem. 1982, 240, 285. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. Ni-catalyzed hydroacylation of alkynes: (e) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. Very recently, efficient Co-catalyzed hydroacylation of alkenes has also been reported: (f) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
36. Rh-catalyzed reaction of aldimines with alkenes: (a) Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489. (b) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200. Ru-catalyzed hydroacylation of alkenes: Isnard, P.; Denise, B.; Sneeden, R. P. A.; Congnion, J. M.; Durual, P. J. Organomet. Chem. 1982, 240, 285. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. Ni-catalyzed hydroacylation of alkynes: (e) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. Very recently, efficient Co-catalyzed hydroacylation of alkenes has also been reported: (f) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
37. Rh-catalyzed reaction of aldimines with alkenes: (a) Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489. (b) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200. Ru-catalyzed hydroacylation of alkenes: Isnard, P.; Denise, B.; Sneeden, R. P. A.; Congnion, J. M.; Durual, P. J. Organomet. Chem. 1982, 240, 285. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. Ni-catalyzed hydroacylation of alkynes: (e) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. Very recently, efficient Co-catalyzed hydroacylation of alkenes has also been reported: (f) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
38. Abbreviations: dppf = 1,1′-bis(diphenylphosphino)ferrocene, dppe = 1,2-biphenylphosphino)ethane, dppp 1,3-bis(diphenylphosphino)propane, dppb = 1,4-bis(diphenylphosphino)butane.
39. Kokubo, K.; Miura, M.; Nomura, M. Organometallics 1995, 14, 4521.
40. Stoichiometric cyclometalation of salicyl aldehydes with Pd, Pt, and Ni is known: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163. (b) Klein, H.-F.; Bickelhaupt, A.; Lemke, M.; Sun, H.; Brand, A.; Jung, T.; Röhr, C.; Flörke, U.; Haupt, H.-J. Organometallics 1997, 16, 668.
41. Stoichiometric cyclometalation of salicyl aldehydes with Pd, Pt, and Ni is known: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163. (b) Klein, H.-F.; Bickelhaupt, A.; Lemke, M.; Sun, H.; Brand, A.; Jung, T.; Röhr, C.; Flörke, U.; Haupt, H.-J. Organometallics 1997, 16, 668.
42. Rhodium-catalyzed reaction of aroyl chlorides with alkynes that may involve alkyne insertion to arylchlorhodium(III) species: Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.