Efficient ruthenium catalyzed transfer hydrogenation of functionalized imines by isopropanol under controlled microwave heating

Canadian Journal of Chemistry

Volumn 83, Issue 6-7, 2005, Pages 909-916

  Samec, Joseph S M ^a   Mony, Laetitia ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Imines; Microwave; Ruthenium; Transfer hydrogenation

Indexed keywords

FREQUENCIES; HYDROGENATION; MICROWAVE HEATING; PROPANE; REACTION KINETICS; RUTHENIUM COMPOUNDS;

IMINES; OIL BATH; TRANSFER HYDROGENATION;

AMINES;

2 PROPANOL; AMINE; FUNCTIONAL GROUP; IMINE; OIL; RUTHENIUM; TOLUENE;

ARTICLE; CATALYSIS; CATALYST; DERIVATIZATION; HEATING; HYDROGENATION; MICROWAVE IRRADIATION; REACTION TIME; TRANSFER HYDROGENATION;

EID: 29244464646     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-103     Document Type: Article

References (34)

1. R.O. Hutchins and M.K. Hutchins. In Comprehensive organic synthesis. Vol. 8. Edited by B.M. Trost and I. Fleming. Pergamon, Oxford. 1991. pp. 25-78.
2. R.C. Larock. Comprehensive organic transformations. WCH, New York. 1989. p. 421.
3. K.A. Schellenberg. J. Org. Chem. 28, 3259 (1963).
4. (a) F. Spindler and H.-U. Blaser. In Transition metals for organic synthesis. Vol. 2. Edited by M. Beller and C. Bolm. Wiley-VCH, Weinheim, Germany. 2004. p. 113;
5. (b) P.N. Rylander. In Hydrogenation methods. Academic Press, New York. 1985. p. 82.
6. S. Gladiali and E. Alberico. In Transition metals for organic synthesis. Vol. 2. Edited by M. Beller and C. Bolm. Wiley-VCH, Weinheim, Germany. 2004. p. 145.
7. (a) G.-Z. Wang and J.-E. Bäckvall. J. Chem. Soc. Chem. Commun. 980 (1992);
8. (b) S. Bhaduri, N. Sapre, K. Sharma, P.G. Jones, and G. Carpenter. J. Chem. Soc. Dalton Trans. 1305 (1990);
9. (c) H.A. Brune, J. Unsin, R. Hemmer, and M. Reichhardt. J. Organomet. Chem. 369, 335 (1989);
10. (d) Y. Watanabe, Y. Tsuji, H. Ige, Y. Ohsugi, and T. Ohta. J. Org. Chem. 49, 3359 (1984);
11. (e) F. Martinelli, G. Mestroni, A. Camus, and G. Zassinovich. J. Organomet. Chem. 220, 383 (1981);
12. (f) R. Grigg, T.R.B. Mitchell, and N. Tongpenyai. Synthesis, 442 (1981).
13. (a) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, and R. Noyori. J. Am. Chem. Soc. 118, 4916 (1996);
14. (b) J. Mao and D.C. Baker. Org. Lett. 1, 841 (1999).
15. J.S.M. Samec and J.-E. Bäckvall. Chem. Eur. J. 8, 2955 (2002).
16. Y. Blum, D. Czarkie, Y. Rahamim, and Y. Shvo. Organometallics, 4, 1459 (1985).
17. (a) N. Menashe and Y. Shvo. Organometallics, 10, 3885 (1991);
18. (b) M.L.S. Almeida, M. Beller, G.-Z. Wang, and J.-E. Bäckvall. Chem. Eur. J. 2, 1533 (1996);
19. (c) G. Csjernyik, A.H. Éll, L. Fadini, B. Pugin, and J.-E. Bäckvall. J. Org. Chem. 67, 1657 (2002);
20. (d) J.H. Choi, N. Kim, Y.J. Shin, J.H. Park, and J. Park. Tetrahedron Lett. 45, 4607 (2004).
21. For the use of 1 as a hydrogen transfer catalyst in racemization, see: (a) O. Pàmies and J.-E. Bäckvall. Chem. Rev. 103, 3247 (2003);
22. (b) M.J. Kim, Y. Ahn, and J. Park. Curr. Opin. Biotechnol. 13, 578 (2002).
23. J.S.M. Samec, A.H. Éll, and J.-E. Bäckvall. Chem. Commun. 2748 (2004).
24. C.P. Casey, S.W. Singer, D.R. Powell, R.K. Hayashi, and M. Kavana. J. Am. Chem. Soc. 123, 1090 (2001)
25. (a) M. Larhed, C. Moberg, and A. Hallberg. Acc. Chem. Res. 35, 717 (2002);
26. (b) A. Svennebring, P. Nilsson, and M. Larhed. J. Org. Chem. 69, 3345 (2004);
27. (c) R-A. Enquist, P. Nilsson, and M. Larhed. Org. Lett. 5, 4875 (2003).
28. P. Lidström, J. Tierney, B. Wathey, and J. Westman. Tetrahedron, 57, 9225 (2001).
29. Y. Niwa and M. Shimizu. J. Am. Chem. Soc. 125, 3720 (2003).
30. I. Ojima, I. Habus, M. Zhao, M. Zucco, Y.H. Park, C.M. Sun, and T. Brigaud. Tetrahedron, 48, 6985 (1992).
31. M.C. Hansen and S.L. Buchwald. Org. Lett. 2, 713 (2000).
32. T. Kawakami, T. Sugimoto, I. Shibata, A. Baba, H. Matsuda, and N. Sonoda. J. Org. Chem. 60, 2677 (1995).
33. E. Aller, R.T. Buck, M.J. Drysdale, L. Ferris, D. Haigh, C.J. Moody, N.D. Pearson, and J.B. Sanghera. J. Chem. Soc. Perkin Trans, 1, 2879 (1996).
34. D.A. Jeyaraj, K.K. Kapoor, V.K. Yadav, H.M. Gauniyal, and M. Parvez. J. Org. Chem. 63, 287 (1998).