Powerful amide synthesis from alcohols and amines under aerobic conditions catalyzed by gold or gold/iron, -nickel or-cobalt nanoparticles

Journal of the American Chemical Society

Volumn 133, Issue 46, 2011, Pages 18550-18553

  Soulé, Jean François ^a   Miyamura, Hiroyuki ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC CONDITION; AMIDE BOND; AMIDE BOND FORMATION; AQUEOUS AMMONIA; SYNTHETIC COMPOUNDS; TERMINAL OXIDANTS;

AMIDES; AMINES; AMINO ACIDS; CATALYST SELECTIVITY; COBALT; COBALT COMPOUNDS; GOLD; MOLECULAR OXYGEN; NANOPARTICLES;

CATALYST ACTIVITY;

ALCOHOL; AMIDE; AMINE; AMINO ACID; AMMONIA; COBALT; GOLD; IRON; NANOPARTICLE; NICKEL; OXIDIZING AGENT; OXYGEN;

AEROBIC REACTOR; AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 83055179288     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2080086     Document Type: Article

References (46)

1. (a) Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd ed.; Wiley-VCH: New York, 1999;
2. (b) Allen, C. L.; Williams, J. M. J. Chem. Soc. Rev. 2011, 40, 3405-3415.
3. Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606-631.
4. Smith, M. B. Compendium of Organic Synthetic Methods; Wiley: New York, 2001; Vol. 9.
5. Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301-312.
6. Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411-420.
7. (a) Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790-792.
8. (b) Naota, T.; Murahashi, S. I. Synlett 1991, 693-694.
9. (a) Nordstrøm, L. U.; Vogt, H.; Madsen, R. J. Am. Chem. Soc. 2008, 130, 17672-17673.
10. (b) Ghosh, S. C.; Muthaiah, S.; Zhang, Y.; Xu, X. Y.; Hong, S. H. Adv. Synth. Catal. 2009, 351, 2643-2649.
11. (c) Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. Org Lett. 2009, 11, 2667-2670.
12. (d) Zweifel, T.; Naubron, J.-V.; Grützmacher, H. Angew. Chem., Int. Ed. 2009, 48, 559-563.
13. (e) Muthaiah, S.; Ghosh, S. C.; Jee, J. E.; Chen, C.; Zhang, J.; Hong, S. H. J. Org Chem. 2010, 75, 3002-3006.
14. (f) Zhang, Y.; Chen, C.; Ghosh, S. C.; Li, Y.; Hong, S. H. Organometallics 2010, 29, 1374-1378.
15. (g) Shimizu, K.; Ohshima, K.; Satsuma, A. Chem.-Eur. J. 2009, 15, 9977-9980.
16. Yoo, W.-J.; Li, C. J. J. Am. Chem. Soc. 2006, 128, 13064-13065.
17. Reddy, K. R.; Maheswari, C. U.; Venkateshwar, M.; Kantam, M. L. Eur. J. Org. Chem. 2008, 3619-3622.
18. Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem. Res. 2005, 38, 851-869.
19. (a) He, L.; Lou, X.-B.; Ni, J.; Liu, Y.-M.; Cao, Y.; He, H.-Y.; Fan, K.-N. Chem.-Eur. J. 2010, 16, 13965-13969.
20. (b) Ishida, T.; Kawakita, N.; Akita, T.; Haruta, M. Gold Bull. 2009, 42, 267-274.
21. Abad, A.; Concepcion, P.; Corma, A.; Garcia, H. Angew. Chem., Int. Ed. 2005, 44, 4066-4069.
22. (a) Prati, L.; Rossi, M. J. Catal. 1998, 176, 552-560.
23. (b) Bianchi, C.; Porta, F.; Prati, L.; Rossi, M. Top. Catal. 2000, 13, 231-236.
24. (c) Carrettin, S.; McMorn, P.; Johnston, P.; Griffin, K.; Hutchings, G. J. Chem. Commun. 2002, 696-697.
25. (d) Tsunoyama, H.; Sakurai, H.; Negishi, Y.; Tsukuda, T. J. Am. Chem. Soc. 2005, 127, 9374-9375.
26. (e) Miyamura, H.; Matsubara, R.; Miyazaki, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2007, 46, 4151-4154.
27. Kegnaes, S.; Mielby, J.; Mentzel, U. V.; Christensen, C. H.; Riisager, A. Green Chem. 2010, 12, 1437-1441.
28. (a) Aschwanden, L.; Mallat, T.; Krumeich, F.; Baiker, A. J. Mol. Catal. A: Chem. 2009, 309, 57-62.
29. (b) Grirrane, A.; Corma, A.; Garcia, H. J. Catal. 2009, 264, 138-144.
30. (c) Miyamura, H.; Morita, M.; Inasaki, T.; Kobayashi, S. Bull. Chem. Soc. Jpn. 2011, 84, 588-599.
31. (d) So, M.-H.; Liu, Y.; Ho, C.-M.; Che, C.-M. Chem. Asian J. 2009, 4, 1551-1561.
32. (e) Zhu, B.; Angelici, R. J. Chem. Commun. 2007, 2157-2159.
33. (a) Klitgaard, S. K.; Egeblad, K.; Mentzel, U. V.; Popov, A. G.; Jensen, T.; Taarning, E.; Nielsen, I. S.; Christensen, C. H. Green Chem. 2008, 10, 419-423.
34. (b) Ishida, T.; Haruta, M. Chem Sus Chem 2009, 2, 538-541.
35. (c) Xu, B.; Zhou, L.; Madix, R. J.; Friend, C. M. Angew. Chem., Int. Ed. 2010, 49, 394-398.
36. (d) Zhou, L.; Freyschlag, C. G.; Xu, B. J.; Friend, C. M.; Madix, R. J. Chem. Commun. 2010, 46, 704-706.
37. (e) Preedasuriyachai, P.; Kitahara, H.; Chavasiri, W.; Sakurai, H. Chem. Lett. 2010, 39, 1174-1176.
38. (a) Miyamura, H.; Yasukawa, T.; Kobayashi, S. Green Chem. 2010, 12, 776-778.
39. (b) Lucchesi, C.; Inasaki, T.; Miyamura, H.; Matsubara, R.; Kobayashi, S. Adv. Synth. Catal. 2008, 350, 1996-2000.
40. (a) Enache, D. I.; Edwards, J. K.; Landon, P.; Solsona-Espriu, B.; Carley, A. F.; Herzing, A. A.; Watanabe, M.; Kiely, C. J.; Knight, D. W.; Hutchings, G. J. Science 2006, 311, 362-365.
41. (b) Tsukuda, T.; Tsunoyama, H.; Sakurai, H. Chem. Asian J. 2011, 6, 736-748.
42. (c) Della Pina, C.; Falletta, E.; Prati, L.; Rossi, M. Chem. Soc. Rev. 2008, 37, 2077-2095.
43. (d) Polshettiwar, V.; Varma, R. S. Green Chem. 2010, 12, 743-754.
44. (a) Landon, P.; Collier, P. J.; Papworth, A. J.; Kiely, C. J.; Hutchings, G. J. Chem. Commun. 2002, 2058-2059.
45. (b) Kaizuka, K.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2010, 132, 15096-15098.
46. (c) Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2011, 133, 3095-3103.