Palladium(II) acetate-catalyzed reduction of imines to the corresponding amines by triethylsilane

Applied Organometallic Chemistry

Volumn 27, Issue 3, 2013, Pages 174-176

  Mirza Aghayan, Maryam ^a   Boukherroub, Rabah ^b   Rahimifard, Mahshid ^a  

^a CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

^b CNRS   (France)

Author keywords

amine compounds; imine compounds; palladium(II) acetate; palladium(II) chloride; reduction; triethylsilane

Indexed keywords

AMINE COMPOUNDS; IMINE COMPOUNDS; PALLADIUM ACETATE; PALLADIUM CHLORIDE; TRIETHYLSILANE;

AMINES; CHLORINE COMPOUNDS; ETHANOL; REDUCTION; VOLATILE FATTY ACIDS;

PALLADIUM COMPOUNDS;

EID: 84874501621     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.2961     Document Type: Article

References (50)

1. H. M. Pinheiro, E. Touraud, O. Thomas, Dyes Pig. 2004, 61, 121.
2. a) K. Iizuka, T. Kamijo, H. Harada, K. Akahane, T. Kubota, H. Umeyama, T. Ishida, Y. Kiso, J. Med. Chem. 1990, 33, 2707
3. b) R. P. Tripathi, N. Saxena, V. K. Tiwari, S. S. Verma, V. Chaturvedi, Y. K. Manju, A. K. Srivastva, A. Gaikwad, S. Sinha, Bioorg. Med. Chem. 2006, 14, 8186.
4. a) S. A. Lawrence, Amines: Synthesis, Properties and Applications, Cambridge University Press, Cambridge, UK, 2004
5. b) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069
6. c) R. O. Hutchins, M. K. Hutchins, Comprehensive Organic Synthesis, Vol. 8 (Eds:, B. M. Trost, I. Fleming,), Pergamon Press, Oxford, 1991, p. 25-74
7. d) S. Bhattacharyya, A. Chatterjee, S. K. Duttachowdhhury, J. Chem. Soc., Perkin Trans. 1 1994, 1
8. e) J. Brussee, R. A. T. M. van Benthem, C. G. Kruse, A. van der Gen, Tetrahedron-Asymmetr. 1990, 1, 163.
9. a) H. Wiener, J. Blum, Y. Sasson, J. Org. Chem. 1991, 56, 4481
10. b) A. Corma, P. Serna, Science 2006, 313, 332
11. c) B. Sreedhar, D. K. Devi, D. Yada, Catal. Commun. 2011, 12, 1009.
12. a) M. Rueping, C. Azap, E. Sugiono, T. Theissmann, Synlett 2005, 2367
13. b) T. Marcelli, P. Hammar, F. Himo, Chem. Eur. J. 2008, 14, 8562
14. c) L. Simón, J. M. Goodman, J. Am. Chem. Soc. 2008, 130, 8741
15. d) C. Zhu, T. Akiyama, Synlett 2011, 1251
16. e) T. C. Nugenta, M. El-Shazlya, Adv. Synth. Catal. 2010, 352, 753.
17. a) J. M. Blackwell, E. R. Sonmor, T. Scoccitti, W. E. Piers, Org. Lett. 2000, 2, 3921
18. b) L. D. Field, B. A. Messerle, S. L. Rumble, Eur. J. Org. Chem. 2005, 2881
19. c) K. A. Kumar, T. S. Sreelekha, K. N. Shivakumara, K. C. Prakasha, D. C. Gowda, Synth. Commun. 2009, 39, 1332
20. d) A. V. Malkov, K. Vrankova, S. Stoncius, P. Kocovsky, J. Org. Chem. 2009, 74, 5839
21. e) A. V. Malkov, K. Vrankova, R. C. Sigerson, S. Stoncius, P. Kocovsky, Tetrahedron 2009, 65, 9481
22. f) H. Hashimoto, I. Aratani, C. Kabuto, M. Kira, Organometallics 2003, 22, 2199
23. g) Y. Nishibayashi, K. Segawa, J. D. Singh, S.-I. Fukuzawa, K. Ohe, S. Uemura, Organometallics 1996, 15, 370
24. h) M. C. Hansen, S. L. Buchwald, Org. Lett. 2000, 2, 713
25. i) B. H. Lipshutz, H. Shimizu, Angew. Chem. Int. Ed. 2004, 43, 2228
26. j) T. Ireland, F. Fontanet, G.-G. Tchao, Tetrahedron Lett. 2004, 45, 4383.
27. B. W. Knettle, R. A. Flowers, Org. Lett. 2001, 3, 2321.
28. a) T. Miyai, M. Ueba, A. Baba, Synlett 1999, 182
29. b) M. Yasuda, Y. Onishi, M. Ueba, T. Miyai, A. Baba, J. Org. Chem. 2001, 66, 7741
30. c) H. Mayr, B. Dogan, Tetrahedron Lett. 1997, 38, 1013
31. d) R. Boukherroub, C. Chatgilialoglu, G. Manuel, Organometallics 1996, 15, 1508
32. e) C. Ferreri, C. Costantino, C. Chatgilialoglu, R. Boukherroub, G. Manuel, J. Organomet. Chem. 1998, 554, 135.
33. a) M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, M. Hoseini, Tetrahedron Lett. 2003, 44, 4579
34. b) M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, Appl. Organomet. Chem. 2006, 20, 214.
35. M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, J. Organomet. Chem. 2005, 690, 2372.
36. M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, M. Rahimifard, J. Organomet. Chem. 2007, 692, 5113.
37. M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, J. Organomet. Chem. 2008, 693, 3567.
38. M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, Tetrahedron Lett. 2009, 50, 5930.
39. M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, R. Zadmard, J. Iran. Chem. Soc. 2011, 8, 570.
40. M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, M. Bolourtchian, Appl. Organomet. Chem. 2010, 24, 477.
41. A. Martínez-Asencio, M. Yus, D. J. Ramón, Synthesis 2011, 3730.
42. A. Martínez-Asencio, D. J. Ramón, M. Yus, Tetrahedron 2011, 67, 3140.
43. J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem. 2000, 65, 1158.
44. K. Fujita, Y. Enoki, R. Yamaguchi, Tetrahedron 2008, 64, 1943.
45. K. Li, P. N. Horton, M. B. Hursthouse, K. K. Hii, J. Organomet. Chem. 2003, 665, 250.
46. D. Guijarro, M. Yus, Tetrahedron 1993, 49, 7761.
47. V. V. Kouznetsov, L. Y. V. Mendez, M. Sortino, Y. Vasquez, M. P. Gupta, M. Freile, R. D. Enriz, S. A. Zacchino, Bioorg. Med. Chem. 2008, 16, 794.
48. F. D. Suvire, M. Sortino, V. V. Kouznetsov, L. Y. Vargas, S. A. Zacchino, U. M. Cruz, R. D. Enriz, Bioorg. Med. Chem. 2006, 14, 1851.
49. O. Saidi, A. J. Blacker, M. M. Farah, S. P. Marsden, J. M. J. Williams, Chem. Commun. 2010, 46, 1541.
50. F. Alonso, P. Riente, M. Yus, Tetrahedron 2009, 65, 10637.