Cationic rhodium complex catalyzed highly selective hydrosilylation of propargylic amine derivatives

Organometallics

Volumn 16, Issue 16, 1997, Pages 3707-3710

  Takeuchi, Ryo ^a   Ebata, Ikuo ^a  

^a YOKOHAMA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001334594     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970219v     Document Type: Article

References (26)

1. For a review, see: (a) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992; p 130. (b) Hiyama, T.; Kusumoto, T. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, p 769. (c) Ojima, I. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1480.
2. For a review, see: (a) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992; p 130. (b) Hiyama, T.; Kusumoto, T. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, p 769. (c) Ojima, I. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1480.
3. For a review, see: (a) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992; p 130. (b) Hiyama, T.; Kusumoto, T. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, p 769. (c) Ojima, I. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 1480.
4. For a review, see: (a) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375. (b) Fleming, I.; Dunogues, J.; Smithers, R. H. Org. React. 1989, 37, 57. (c) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988; p 7.
5. For a review, see: (a) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375. (b) Fleming, I.; Dunogues, J.; Smithers, R. H. Org. React. 1989, 37, 57. (c) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988; p 7.
6. For a review, see: (a) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375. (b) Fleming, I.; Dunogues, J.; Smithers, R. H. Org. React. 1989, 37, 57. (c) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988; p 7.
7. For example, see: Lewis, L. N.; Sy, K. G.; Brayant, G. L.; Donahue, P. E. Organometallics 1991, 10, 3750.
8. (a) Takeuchi, R.; Nitta, S.; Watanabe, D. J. Org. Chem. 1995, 60, 3045.
9. (b) Takeuchi, R.; Nitta, S.; Watanabe, D. J. Chem. Soc., Chem. Commun. 1994, 1777.
10. (c) Takeuchi, R.; Tanouchi, N. J. Chem. Soc., Perkin Trans. 1 1994, 2909.
11. (d) Takeuchi, R.; Tanouchi, N. J. Chem. Soc., Chem. Commun. 1993, 1319.
12. Neutral rhodium complex catalyzed hydrosilylation of 1-alkynes is (Z)-selective, see: Ojima, I; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127.
13. For example, see: Takeuchi, R.; Sugiura, M. J. Chem. Soc., Perkin Trans. 1 1993, 1031.
14. (a) Pukhnarevich, V. B.; Kopylova, L. I.; Trofimov, B. A.; Voronkov, M. G. Zh. Obshch. Khim. 1975, 45, 89.
15. (b) Lukevics, E.; Pestunovich, A. E.; Pestunovich, V. A.; Liepinsh, E. E.; Voronkov, M. G. Zh. Obshch. Khim. 1971, 41, 1585.
16. (c) Lukevics, E.; Pestunovich, A. E.; Pestunovich, V. A.; Voronkov, M. G. Zh. Obshch. Khim. 1970, 40, 624.
17. Polymerization of arylalkynes in the presence of hydrosilane has been reported, see: (a) Goldberg, Y.; Alper, H. J. Chem. Soc., Chem. Commun. 1994, 1209. (b) Yamamoto, H.; Mondoh, K.; Fuchikami, T. Tetrahedron Lett. 1994, 35, 4137. Rhodium complex catalyzed polymerization of alkynes, see: (c) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 12131. (d) Amer, I.; Schumann, H.; Ravindar, V.; Baidossi, W.; Goren, N.; Blum, J. J. Mol. Catal. 1993, 85, 163.
18. Polymerization of arylalkynes in the presence of hydrosilane has been reported, see: (a) Goldberg, Y.; Alper, H. J. Chem. Soc., Chem. Commun. 1994, 1209. (b) Yamamoto, H.; Mondoh, K.; Fuchikami, T. Tetrahedron Lett. 1994, 35, 4137. Rhodium complex catalyzed polymerization of alkynes, see: (c) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 12131. (d) Amer, I.; Schumann, H.; Ravindar, V.; Baidossi, W.; Goren, N.; Blum, J. J. Mol. Catal. 1993, 85, 163.
19. Polymerization of arylalkynes in the presence of hydrosilane has been reported, see: (a) Goldberg, Y.; Alper, H. J. Chem. Soc., Chem. Commun. 1994, 1209. (b) Yamamoto, H.; Mondoh, K.; Fuchikami, T. Tetrahedron Lett. 1994, 35, 4137. Rhodium complex catalyzed polymerization of alkynes, see: (c) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 12131. (d) Amer, I.; Schumann, H.; Ravindar, V.; Baidossi, W.; Goren, N.; Blum, J. J. Mol. Catal. 1993, 85, 163.
20. Polymerization of arylalkynes in the presence of hydrosilane has been reported, see: (a) Goldberg, Y.; Alper, H. J. Chem. Soc., Chem. Commun. 1994, 1209. (b) Yamamoto, H.; Mondoh, K.; Fuchikami, T. Tetrahedron Lett. 1994, 35, 4137. Rhodium complex catalyzed polymerization of alkynes, see: (c) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 12131. (d) Amer, I.; Schumann, H.; Ravindar, V.; Baidossi, W.; Goren, N.; Blum, J. J. Mol. Catal. 1993, 85, 163.
21. (a) Speier, J. L. Adv. Organomet. Chem. 1979, 17, 407.
22. (b) Reference 1a, p 41.
23. Reference 1a, p 160.
24. Schenck, T. G.; Downs, J. M.; Milne, C. R. C.: Mackenzie, P. B.; Boucher, H.; Whealan, J.; Bosnieh, B. Inorg. Chem. 1985, 24, 2334.
25. Osborn, J. A.; Wilkinson, G. Inorg. Synth. 1967, 10, 67.
26. Giordano, G.; Crabtree, R. H. Inorg. Synth. 1979, 19, 218.