Catalytic oxidative synthesis of nitriles directly from primary alcohols and ammonia

Angewandte Chemie - International Edition

Volumn 48, Issue 34, 2009, Pages 6286-6288

  Oishi, Takamichi ^a   Yamaguchi, Kazuya ^a,b   Mizuno, Noritaka ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Alcohols; Ammonia; Heterogeneous catalysis; Nitriles; Ruthenium

Indexed keywords

CATALYTIC PERFORMANCE; HETEROGENEOUS CATALYSIS; HETEROGENEOUS CATALYST; NITRILES; PRIMARY ALCOHOLS;

ALDEHYDES; AMMONIA; CATALYSTS; CYANIDES; RUTHENIUM;

CATALYSIS;

ALCOHOL DERIVATIVE; AMMONIA; NITRILE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALCOHOLS; AMMONIA; CATALYSIS; NITRILES; OXIDATION-REDUCTION; RUTHENIUM;

EID: 70349935280     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900418     Document Type: Article

References (44)

1. a) A. J. Fatiadi in Preparation and Synthetic Applications of Cyano Compounds (Eds.: S. Patai, Z. Rappaport), Wiley, New York, 1983;
2. b) J. S. Miller, J. L. Manson, Acc. Chem. Res. 2001, 34, 563;
3. c) P. Magnus, D. A. Scott, M. R. Fielding, TetrahedronLett. 2001, 42, 4127;
4. d) M. B. Smith, J. March, March's AdvancedOrganic Chemistry: Reactions, Mechanisms, and Structure, 6thed., Wiley, Hoboken, NJ, 2007.
5. a) P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, London, 1998;
6. b) R. A. Sheldon, Green Chem. 2000, 2, G1;
7. c) P. T. Anastas, L. B. Bartlett, M. M. Kirchhoff, T. C. Williamson, Catal. Today 2000, 55, 11.
8. a) K. Ishihara, Y. Furuya, H. Yamamoto, Angew. Chem. 2002, 114, 3109;
9. Angew. Chem. Int. Ed. 2002, 41, 2983;
10. b) P. Yan, P. Batamack, G. K. S. Prakash, G. A. Olah, Catal. Lett. 2005, 101, 141;
11. c) S. H. Yang, S. Chang, Or g. Lett. 2001, 3, 4209;
12. d) E. Choi, C. Lee, Y. Na, S. Chang, Org. Lett. 2002, 4, 2369;
13. e) K. Yamaguchi, H. Fujiwara, Y. Ogasawara, M. Kotani, N. Mizuno, Angew. Chem. 2007, 119, 3996;
14. Angew. Chem. Int. Ed. 2007, 46, 3922.
15. a) S. Iida, H. Togo, Tetrahedron 2007, 63, 8274;
16. b) N Mori, H. Togo, Synlett 2005, 1456;
17. c) S. Iida, H. Tago, Synlett 2007, 407;
18. d) S. Yamazaki, Y. Yamazaki, Chem. Lett. 1990, 571;
19. e) G. D. McAllister, C. D. Wilfred, R. J. K. Taylor, Synlett 2002, 1291;
20. f) F.-E. Chen, Y.-Y. Li, H.-Q. Jia, Synthesis 2002, 1804.
21. [5b] from alcohols using gaseous ammonia (typically 7.5 atm) and liquid ammonia, respectively, have been reported: a) C. Gunanathan, D. Milstein, Angew. Chem. 2008, 120, 8789;
22. Angew. Chem. Int. Ed. 2008, 47, 8661;
23. b) T. Zweifel, J.-V. Naubron, H. Grützmacher, Angew. Chem. 2009, 121, 567;
24. Angew. Chem. Int. Ed. 2009, 48, 559.
25. a) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720;
26. Angew. Chem. Int. Ed. 2002, 41, 4538;
27. b) K. Yamaguchi, N. Mizuno, Chem. Eur. J. 2003, 9, 4353;
28. c) K. Yamaguchi, N. Mizuno, Angew. Chem. 2003, 115, 1518;
29. Angew. Chem. Int. Ed. 2003, 42, 1480;
30. d) J. W. Kim, K. Yamaguchi, N. Mizuno, Angew. Chem. 2008, 120, 9389;
31. Angew. Chem. Int. Ed. 2008, 47, 9249;
32. e) K. Yamaguchi, T. Koike, J. W. Kim, Y. Ogasawara, N. Mizuno, Chem. Eur. J. 2008, 14, 11480.
33. The gas-phase ammoxidations of small alcohols (reaction temperature ≤350°C) have been reported: a) B. M. Reddy, B. Manohar, J. Chem. Soc. Chem. Commun. 1993, 234;
34. b) S. J. Kulkarni, R. R. Rao, M. Subrahmanyam, A. V. R. Rao, J. Chem. Soc. Chem. Commun. 1994, 237.
35. The development of easily recovered and recycled heterogeneous catalysts, especially for oxidation reactions, has received interest and can solve the problems associated with the homogeneous systems: a) R. A. Sheldon, H. van Bekkum, Fine Chemical through Heterogeneous Catalysis, Wiley, Weinheim, 2001;
36. b) G Centi, F. Cavani, F. Trifiro, Selective Oxidation by Heterogeneous Catalysis, Kluwer, New York, 2001;
37. c) I. V. Kozhevnikov, NATO Science Series, II: Mathematics, Physics and Chemistry, Kluwer, New York, 2003, pp. 351-380;
38. d) B. Warren, S. T Oyama, Heterogeneous Hydrocarbon Oxidation, ACS, Washington, DC, 1996;
39. e) A. Bhan, E. Iglesia, Acc. Chem. Res. 2008, 41, 559.
40. K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2000, 122, 7144.
41. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485.
42. K. Yamaguchi, M. Matsushita, N. Mizuno, Angew. Chem. 2004, 116, 1602;
43. Angew. Chem. Int. Ed. 2004, 43, 1576.
44. +], 154 (92), 153 (18), 128 (32), 127 (44), 126 (18), 77 (18)) albeit in an only small amount (below 1 % yield).