Selective Lactam Formation from Amino Alcohols Using Polymer-Incarcerated Gold and Gold/Cobalt Nanoparticles as Catalysts under Aerobic Oxidative Conditions

Asian Journal of Organic Chemistry

Volumn 1, Issue 4, 2012, Pages 319-321

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Gold nanoparticles; Heterogeneous catalysis; Lactams; Oxidation; Oxygen

Indexed keywords

EID: 84880818812     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201200093     Document Type: Article

References (37)

1. J. A. Gladysz, Chem. Rev. 2002, 102, 3215-3216;
2. V. Polshettiwar, J.-M. Basset, D. Astruc, ChemSusChem 2012, 5, 6-8;
3. V. Polshettiwar, R. S. Varma, Green Chem. 2010, 12, 743-754.
4. R. A. Sheldon, I. W. C. E. Arends, G.-J. tenBrink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774-781.
5. S. Kobayashi, H. Miyamura, Chem. Rec. 2010, 10, 271-290;
6. R. Akiyama, S. Kobayashi, Chem. Rev. 2009, 109, 594-642.
7. H. Miyamura, R. Matsubara, Y. Miyazaki, S. Kobayashi, Angew. Chem. 2007, 119, 4229-4232; Angew. Chem. Int. Ed. 2007, 46, 4151-4154;
8. C. Lucchesi, T. Inasaki, H. Miyamura, R. Matsubara, S. Kobayashi, Adv. Synth. Catal. 2008, 350, 1996-2000;
9. H. Miyamura, R. Matsubara, S. Kobayashi, Chem. Commun. 2008, 2031-2033.
10. H. Miyamura, M. Shiramizu, R. Matsubara, S. Kobayashi, Chem. Lett. 2008, 37, 360-361.
11. H. Miyamura, M. Morita, T. Inasaki, S. Kobayashi, Bull. Chem. Soc. Jpn. 2011, 84, 588-599.
12. H. Miyamura, T. Yasukawa, S. Kobayashi, Green Chem. 2010, 12, 776-778;
13. T. Yasukawa, H. Miyamura, S. Kobayashi, Chem. Asian J. 2011, 6, 621-627;
14. K. Kaizuka, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2010, 132, 15096-15098.
15. W.-J. Yoo, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 3095-3103.
16. J.-F. Soulé, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 18550-18553.
17. R. C. Larock, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nded., Wiley-VCH, New York, 1999;
18. P. Camilleri, R. Ellul, A. J. Kirby, T. G. Mujahid, J. Chem. Soc. Perkin Trans. 2 1979, 1617-1620.
19. M. Hashimoto, Y. Obora, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2008, 73, 2894-2897;
20. H. Sharghi, M. Hosseini, Synthesis 2002, 1057-1060;
21. Y. Izumi, S. Sato, K. Urabe, Chem. Lett. 1983, 12, 1649-1652.
22. P. A. S. Smith, J. Am. Chem. Soc. 1948, 70, 320-323.
23. T. Naota, S. I. Murahashi, Synlett 1991, 693-694.
24. K. Fujita, Y. Takahashi, M. Owaki, K. Yamamoto, R. Yamaguchi, Org. Lett. 2004, 6, 2785-2788.
25. S. Kegnæs, J. Mielby, U. V. Mentzel, C. H. Christensen, A. Riisager, Green Chem. 2010, 12, 1437-1441.
26. For some representative examples of direct amide formation by dehydrogenation processes, see:
27. C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790-792;
28. S. C. Ghosh, S. Muthaiah, Y. Zhang, X. Y. Xu, S. H. Hong, Adv. Synth. Catal. 2009, 351, 2643-2649;
29. T. Zweifel, J.-V. Naubron, H. Grützmacher, Angew. Chem. 2009, 121, 567-571; Angew. Chem. Int. Ed. 2009, 48, 559-563;
30. A. J. A. Watson, A. C. Maxwell, J. M. J. Williams, Org. Lett. 2009, 11, 2667-2670;
31. Y. Zhang, C. Chen, S. C. Ghosh, Y. Li, S. H. Hong, Organometallics 2010, 29, 1374-1378;
32. C. Chen, S. H. Hong, Org. Biomol. Chem. 2011, 9, 20-26, and references therein.
33. For some representative examples of direct amide formation by TOPs, see:
34. Y. Wang, D. Zhu, L. Tang, S. Wang, Z. Wang, Angew. Chem. 2011, 123, 9079-9083; Angew. Chem. Int. Ed. 2011, 50, 8917-8921;
35. J. Zhu, Y. Zhang, F. Shi, Y. Deng, Tetrahedron Lett. 2012, 53, 3178-3180.
36. The base as well as the amount of base was already screened in the intermolecular reaction, see Ref.[9].
37. P. Dubois, O. Coulembier, J. M. Raquez, Handbook of Ring-Opening Polymerization, Wiley, 2009.