Trichlorosilane-dimethylformamide (Cl3SiH-DMF) as an efficient reducing agent. Reduction of aldehydes and imines and reductive amination of aldehydes under mild conditions using hypervalent hydridosilicates

Chemistry Letters

Volumn , Issue 5, 1996, Pages 407-408

  Kobayashi, Shu ^a   Yasuda, Masaru ^a   Hachiya, Iwao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010158798     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.407     Document Type: Article

References (19)

1. M. Hudlicky, "Reduction in Organic Chemistry," Ellis Horwood Limited, Chichester (1984).
2. R. A. Benkeser and W. E. Smith, J. Am. Chem. Soc., 91, 1556 (1969).
3. R. A. Benkeser and D. C. Snyder, J. Organomet. Chem., 225, 107 (1982).
4. M. Kira, K. Sato, and H. Sakurai, J. Org. Chem., 52, 949 (1987).
5. S. Kobayashi and K. Nishio, J. Org. Chem., 59, 6620 (1994).
6. S. Kobayashi and K. Nishio, J. Am. Chem. Soc., 117, 6392 (1995).
7. For example, M, Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990); M. Fujita and T. Hiyama, J. Org. Chem., 53, 5405 (1988); G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, M. Kobayashi, and H. Sakurai, Tetrahedron Lett., 28, 4081 (1987).
8. For example, M, Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990); M. Fujita and T. Hiyama, J. Org. Chem., 53, 5405 (1988); G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, M. Kobayashi, and H. Sakurai, Tetrahedron Lett., 28, 4081 (1987).
9. For example, M, Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990); M. Fujita and T. Hiyama, J. Org. Chem., 53, 5405 (1988); G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, M. Kobayashi, and H. Sakurai, Tetrahedron Lett., 28, 4081 (1987).
10. For example, M, Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990); M. Fujita and T. Hiyama, J. Org. Chem., 53, 5405 (1988); G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, M. Kobayashi, and H. Sakurai, Tetrahedron Lett., 28, 4081 (1987).
11. For example, M, Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990); M. Fujita and T. Hiyama, J. Org. Chem., 53, 5405 (1988); G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, M. Kobayashi, and H. Sakurai, Tetrahedron Lett., 28, 4081 (1987).
12. 2. After a usual work up, the corresponding alcohols were obtained.
13. For reductive amination using borohydrides, A. F. Abdel-Magid, C. A. Maryanoff, and K. G. Carson, Tetrahedron Lett., 31, 5595 (1990); R. F. Borch, M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc., 93, 2897 (1971).
14. For reductive amination using borohydrides, A. F. Abdel-Magid, C. A. Maryanoff, and K. G. Carson, Tetrahedron Lett., 31, 5595 (1990); R. F. Borch, M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc., 93, 2897 (1971).
15. 2. After a usual work up, the corresponding amines were obtained.
16. Measured at 20 °C (0.25 M).
17. H. Marsmann, in "NMR, Oxygen-17 and Silicon-29," ed by P. Diehl, E. Fluck, and R. Kosfeld, Springer-Verlag, Berlin (1981), Vol. 17, p. 65; J. A. Cella, J. D. Cargiolo, and E. A. Williams, J. Organomet. Chem., 186, 13 (1980).
18. H. Marsmann, in "NMR, Oxygen-17 and Silicon-29," ed by P. Diehl, E. Fluck, and R. Kosfeld, Springer-Verlag, Berlin (1981), Vol. 17, p. 65; J. A. Cella, J. D. Cargiolo, and E. A. Williams, J. Organomet. Chem., 186, 13 (1980).
19. The signal at -184.6 ppm was confirmed by comparison with that of the authentic sample prepaed from 3-phenylpropanol, triethylamine, and tetrachlorosilane.