A practical procedure for reduction of primary, secondary and tertiary amides to amines

Advanced Synthesis and Catalysis

Volumn 355, Issue 1, 2013, Pages 47-52

  Reeves, Jonathan T ^a   Tan, Zhulin ^a   Marsini, Maurice A ^a   Han, Zhengxu S ^a   Xu, Yibo ^a   Reeves, Diana C ^a   Lee, Heewon ^a   Lu, Bruce Z ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

amides; reduction; ruthenium; silanes

Indexed keywords

EID: 84872202267     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200835     Document Type: Article

References (39)

1. Reductions in Organic Chemistry, (Ed.:, M. Hudlicky,), John Wiley & Sons, New York, 1984
2. Comprehensive Organic Synthesis, Vol. 8, (Eds.:, B.M. Trost, I. Fleming,), Pergamon, Oxford, U.K., 1991
3. Modern Reduction Methods, (Eds.:, P.G. Andersson, I.J. Munslow,), Wiley, New York, 2008.
4. J. Seyden-Penne, Reductions by the Alumino and Borohydrides in Organic Synthesis, 2nd edn., Wiley, New York, 1997
5. G. W. Gribble, Chem. Soc. Rev. 1998, 27, 395-404.
6. R. Calas, E. Frainnet, A. Bazouin, Compt. Rend. 1962, 254, 2357-2359
7. E. Frainnet, A. Bazouin, R. Calas, Compt. Rend. 1963, 257, 1304-1306
8. R. Calas, Pure Appl. Chem. 1966, 13, 61-79
9. R. Calas, J. Organomet. Chem. 1980, 200, 11-36.
10. R. Kuwano, M. Takahashi, Y. Ito, Tetrahedron Lett. 1998, 39, 1017-1020.
11. M. Igarashi, T. Fuchikami, Tetrahedron Lett. 2001, 42, 1945-1947.
12. H. Nagashima, A. Suzuki, T. Iura, K. Ryu, K. Matsubara, Organometallics 2000, 19, 3579-3590
13. K. Matsubara, T. Iura, T. Maki, H. Nagashima, J. Org. Chem. 2002, 67, 4985-4988
14. Y. Motoyama, K. Mitsui, T. Ishida, H. Nagashima, J. Am. Chem. Soc. 2005, 127, 13150-13151
15. S. Hanada, Y. Motoyama, H. Nagashima, Tetrahedron Lett. 2006, 47, 6173-6177
16. S. Hanada, T. Ishida, Y. Motoyama, H. Nagashima, J. Org. Chem. 2007, 72, 7551-7559
17. H. Sasakuma, Y. Motoyama, H. Nagashima, Chem. Commun. 2007, 4916-4918
18. S. Hanada, E. Tsutsumi, Y. Motoyama, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 15032-15040.
19. S. Zhou, K. Junge, D. Addis, S. Das, M. Beller, Angew. Chem. 2009, 121, 9671-9674
20. Angew. Chem. Int. Ed. 2009, 48, 9507-9510
21. Y. Sunada, H. Kawakami, T. Imaoka, Y. Motoyama, H. Nagashima, Angew. Chem. 2009, 121, 9675-9678
22. Angew. Chem. Int. Ed. 2009, 48, 9511-9514.
23. S. Das, D. Addis, S. Zhou, K. Junge, M. Beller, J. Am. Chem. Soc. 2010, 132, 1770-1771
24. S. Das, D. Addis, S. Zhou, K. Junge, M. Beller, J. Am. Chem. Soc. 2010, 132, 4971.
25. S. Das, D. Addis, K. Junge, M. Beller, Chem. Eur. J. 2011, 17, 12186-12192.
26. S. Das, B. Join, K. Junge, M. Beller, Chem. Commun. 2012, 48, 2683-2685.
27. G. Barbe, A. B. Charette, J. Am. Chem. Soc. 2008, 130, 18-19.
28. G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc. 2010, 132, 12817-12819.
29. S.-H. Xiang, J. Xu, H.-Q. Yuan, P.-Q. Huang, Synlett 2010, 12, 1829-1832.
30. S. Laval, W. Dayoub, L. Pehlivan, E. Metay, A. Favre-Reguillon, D. Delbrayelle, G. Mignani, M. Lemaire, Tetrahedron Lett. 2011, 52, 4072-4075.
31. S. Das, B. Wendt, K. Möller, K. Junge, M. Beller, Angew. Chem. 2012, 124, 1694-1698
32. Angew. Chem. Int. Ed. 2012, 51, 1662-1666.
33. S. Park, M. Brookhart, J. Am. Chem. Soc. 2012, 134, 640-653.
34. C. Cheng, M. Brookhart, J. Am. Chem. Soc. 2012, 134, 11304-11307.
35. K. Rehse, G. Claus, S. Leiβring, Arch. Pharm. 1987, 320, 1155-1161.
36. S. Hanada, Y. Motoyama, H. Nagashima, Eur. J. Org. Chem. 2008, 4097-4100.
37. S. Zhou, D. Addis, S. Das, K. Junge, M. Beller, Chem. Commun. 2009, 4883-4885
38. S. Zhou, K. Junge, D. Addis, S. Das, M. Beller, Org. Lett. 2009, 11, 2461-2464.
39. G. Bijukumar, B. Maloyesh, B. S. Bhaskar, A. Rajendra, Synth. Commun. 2008, 38, 1512-1517.