Oxidant-free conversion of primary amines to nitriles

Journal of the American Chemical Society

Volumn 135, Issue 44, 2013, Pages 16352-16355

  Tseng, Kuei Nin T ^a   Rizzi, Andrew M ^a   Szymczak, Nathaniel K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SYSTEM; CHEMOSELECTIVE; DIHYDROGEN; HYDRIDE COMPLEXES; PRIMARY AMINES; PRIMARY AND SECONDARY AMINE;

CYANIDES; DEHYDROGENATION; OXIDANTS;

AMINES;

AMINE; HYDROGEN; IMINE; NITRILE;

ARTICLE; CATALYSIS; CATALYST; DEHYDROGENATION;

AMINES; CATALYSIS; MOLECULAR STRUCTURE; NITRILES; ORGANOMETALLIC COMPOUNDS;

EID: 84887708293     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409223a     Document Type: Article

References (70)

1. Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597
2. Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. J. Med. Chem. 2010, 53, 7902
3. Pollak, P.; Romeder, G.; Hagedorn, F.; Gelbke, H.-P. Nitriles. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, Germany, 2012.
4. Srimani, D.; Feller, M.; Ben-David, Y.; Milstein, D. Chem. Commun. 2012, 48, 11853
5. Gunanathan, C.; Hoelscher, M.; Leitner, W. Eur. J. Inorg. Chem. 2011, 2011, 3381
6. Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379
7. Sandmeyer, T. Ber. Dtsch. Chem. Ges. 1885, 18, 1496
8. Sandmeyer, T. Ber. Dtsch. Chem. Ges. 1885, 18, 1492
9. Rosenmund, K. W.; Struck, E. Ber. Dtsch. Chem. Ges. 1919, 52, 1749
10. Yamaguchi, K.; Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Mizuno, N. Angew. Chem., Int. Ed. 2007, 46, 3922
11. Ishihara, K.; Furuya, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2983
12. Chakraborty, S.; Patel, Y. J.; Krause, J. A.; Guan, H. Angew. Chem., Int. Ed. 2013, 52, 1
13. Falk, A.; Goederz, A.-L.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2013, 52, 1576
14. Velcicky, J.; Soicke, A.; Steiner, R.; Schmalz, H.-G. J. Am. Chem. Soc. 2011, 133, 6948
15. Laulhe, S.; Gori, S. S.; Nantz, M. H. J. Org. Chem. 2012, 77, 9334
16. Kamijo, S.; Hoshikawa, T.; Inoue, M. Org. Lett. 2011, 13, 5928
17. Lamani, M.; Prabhu, K. R. Angew. Chem., Int. Ed. 2010, 49, 6622
18. Oishi, T.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2009, 48, 6286
19. Rajender Reddy, K.; Uma Maheswari, C.; Venkateshwar, M.; Prashanthi, S.; Lakshmi Kantam, M. Tetrahedron Lett. 2009, 50, 2050
20. Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. Org. Lett. 2009, 11, 2461
21. Grasselli, R. K. Catal. Today 1999, 49, 141
22. Murahashi, S.-I.; Imada, Y. Amine Oxidation. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2008; pp 497.
23. Porta, F.; Crotti, C.; Cenini, S.; Palmisano, G. J. Mol. Catal. 1989, 50, 333
24. Green, G.; Griffith, W. P.; Hollinshead, D. M.; Ley, S. V.; Schroder, M. J. Chem. Soc. Perkin Trans. 1 1984, 681
25. Lee, J. B.; Parkin, C.; Shaw, M. J.; Hampson, N. A.; Macdonald, K. I. Tetrahedron 1973, 29, 751
26. Clarke, T. G.; Hampson, N. A.; Lee, J. B.; Morley, J. R.; Scanlon, B. Tetrahedron Lett. 1968, 9, 5685
27. Stojiljković, A.; Andrejević, V.; Mihailovi, M. L. Tetrahedron 1967, 23, 721
28. Nicolaou, K. C.; Mathison, C. J. N. Angew. Chem., Int. Ed. 2005, 44, 5992
29. P. Griffith, W.; Reddy, B.; G. F. Shoair, A.; Suriaatmaja, M.; J. P. White, A.; J. Williams, D. J. Chem. Soc., Dalton Trans. 1998, 2819
30. Yamazaki, S.; Yamazaki, Y. Bull. Chem. Soc. Jpn. 1990, 63, 301
31. Kim, J.; Stahl, S. S. ACS Catal. 2013, 3, 1652
32. Aiki, S.; Taketoshi, A.; Kuwabara, J.; Koizumi, T.-a.; Kanbara, T. J. Organomet. Chem. 2011, 696, 1301
33. Zhang, Y.; Xu, K.; Chen, X.; Hu, T.; Yu, Y.; Zhang, J.; Huang, J. J. Catal. Commun. 2010, 11, 951
34. Maeda, Y.; Nishimura, T.; Uemura, S. Bull. Chem. Soc. Jpn. 2003, 76, 2399
35. Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2003, 42, 1480
36. Mori, K.; Yamaguchi, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 2001, 461
37. Bailey, A. J.; James, B. R. Chem. Commun. 1996, 2343
38. Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc. Chem. Commun. 1978, 562
39. Nielsen, M.; Alberico, E.; Baumann, W.; Drexler, H.-J.; Junge, H.; Gladiali, S.; Beller, M. Nature 2013, 495, 85
40. Rodriguez-Lugo, R. E.; Trincado, M.; Vogt, M.; Tewes, F.; Santiso-Quinones, G.; Grutzmacher, H. Nature Chem. 2013, 5, 342
41. Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2012, 51, 2772
42. Nielsen, M.; Junge, H.; Kammer, A.; Beller, M. Angew. Chem., Int. Ed. 2012, 51, 5711
43. Marr, A. C. Catal. Sci. Technol. 2012, 2, 279
44. Prades, A.; Peris, E.; Albrecht, M. Organometallics 2011, 30, 1162
45. Johnson, T. C.; Morris, D. J.; Wills, M. Chem. Soc. Rev. 2010, 39, 81
46. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681
47. Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc. Chem. Commun. 1979, 870
48. Bernskoetter, W. H.; Brookhart, M. Organometallics 2008, 27, 2036
49. Wang, Z.; Belli, J.; Jensen, C. M. Faraday Discuss. 2011, 151, 297
50. Gu, X.-Q.; Chen, W.; Morales-Morales, D.; Jensen, C. M. J. Mol. Catal. A: Chem. 2002, 189, 119
51. Tseng, K.-N. T.; Kampf, J. W.; Szymczak, N. K. Organometallics 2013, 32, 2046
52. Wu, J.; Talwar, D.; Johnston, S.; Yan, M.; Xiao, J. Angew. Chem., Int. Ed. 2013, 52, 6983
53. Schumperli, M. T.; Hammond, C.; Hermans, I. ACS Catal. 2012, 2, 1108
54. Luca, O. R.; Wang, T.; Konezny, S. J.; Batista, V. S.; Crabtree, R. H. New J. Chem. 2011, 35, 998
55. Yi, C. S.; Lee, D. W. Organometallics 2009, 28, 947
56. Kitamura, M.; Noyori, R. Hydrogenation and Transfer Hydrogenation. In Ruthenium in Organic Synthesis; Murahashi, S.-I., Eds.; Wiley-VCH: Weinheim, Germany, 2005; pp 3.
57. Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed 1998, 37, 1703
58. Murahashi, S.; Naota, T.; Ito, K.; Maeda, Y.; Taki, H. J. Org. Chem. 1987, 52, 4319
59. Hallman, P. S.; McGarvey, B. R.; Wilkinson, G. J. Chem. Soc. A 1968, 3143
60. Muthaiah, S.; Hong, S. H. Adv. Synth. Catal. 2012, 354, 3045
61. Blum, Y.; Shvo, Y. J. Organomet. Chem. 1985, 282, C7
62. Conley, B. L.; Pennington-Boggio, M. K.; Boz, E.; Williams, T. J. Chem. Rev. 2010, 110, 2294
63. Hollmann, D.; Haijun, J.; Spannerberg, A.; Bahn, S.; Tillack, A.; Parton, R.; Altink, R.; Beller, M. Organometallics 2009, 28, 473
64. Jung, C. W.; Fellmann, J. D.; Garrou, P. E. Organometallics 1983, 2, 1042
65. Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press; Boca Raton, FL, 1991; pp 203.
66. Crabtree, R. H. Chem. Rev. 2012, 112, 1536
67. Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem 2003, 198, 317
68. Bayram, E.; Finke, R. G. ACS Catalysis 2012, 2, 1967
69. Note that primary aldimines are unstable under our reaction conditions, see reference: Lee, J. H.; Gupta, S.; Jeong, W.; Rhee, Y. H.; Park, J. Angew. Chem., Int. Ed. 2012, 51, 10851
70. Crabtree, R. H. Energy Environ. Sci. 2008, 1, 134