Direct amidation from alcohols and amines through a tandem oxidation process catalyzed by heterogeneous-polymer-incarcerated gold nanoparticles under aerobic conditions

Chemistry - An Asian Journal

Volumn 8, Issue 11, 2013, Pages 2614-2626

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

alcohols; amides; heterogeneous catalysis; nanoparticles; oxidation

Indexed keywords

AEROBIC CONDITION; GOLD NANOPARTICLES; HETEROGENEOUS CATALYST; HIGH SELECTIVITY; OXIDATION PROCESS; SIMPLE OPERATION; SYNTHESIS OF AMIDE; TERMINAL OXIDANTS;

ALCOHOLS; AMIDES; AMINES; CATALYSIS; CATALYST SELECTIVITY; METAL NANOPARTICLES; NANOPARTICLES; OXIDATION; OXIDATION RESISTANCE; STYRENE; SUBSTRATES; SYNTHESIS (CHEMICAL);

GOLD;

EID: 84887024215     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201300733     Document Type: Article

References (110)

1. R. C. Larock, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2 nd ed., Wiley-VCH, New York, 1999
2. M. B. Smith, Compendium of Organic Synthetic Methods, Vol. 9, 2001.
3. E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606-631
4. K. Ishihara, S. Ohara, H. Yamamoto, J. Org. Chem. 1996, 61, 4196-4197
5. R. M. Al-Zoubi, O. Marion, D. G. Hall, Angew. Chem. 2008, 120, 2918-2921
6. Angew. Chem. Int. Ed. 2008, 47, 2876-2879
7. H. Charville, D. Jackson, G. Hodges, A. Whiting, Chem. Commun. 2010, 46, 1813-1823
8. C. L. Allen, B. N. Atkinson, J. M. J. Williams, Angew. Chem. 2012, 124, 1412-1415
9. Angew. Chem. Int. Ed. 2012, 51, 1383-1386.
10. V. R. Pattabiraman, J. W. Bode, Nature 2011, 480, 471-479.
11. D. Crich, K. Sasaki, Org. Lett. 2009, 11, 3514-3517
12. P. Dawson, T. Muir, I. Clark-Lewis, S. Kent, Science 1994, 266, 776-779
13. D. Crich, I. Sharma, Angew. Chem. 2009, 121, 2391-2394
14. Angew. Chem. Int. Ed. 2009, 48, 2355-2358
15. R. V. Kolakowski, N. Shangguan, R. R. Sauers, L. J. Williams, J. Am. Chem. Soc. 2006, 128, 5695-5702
16. N. Shangguan, S. Katukojvala, R. Greenberg, L. J. Williams, J. Am. Chem. Soc. 2003, 125, 7754-7755
17. R. Merkx, A. J. Brouwer, D. T. S. Rijkers, R. M. J. Liskamp, Org. Lett. 2005, 7, 1125-1128.
18. P.-C. Chiang, Y. Kim, J. W. Bode, Chem. Commun. 2009, 0, 4566-4568.
19. B. Shen, D. M. Makley, J. N. Johnston, Nature 2010, 465, 1027-1032.
20. S. H. Cho, E. J. Yoo, I. Bae, S. Chang, J. Am. Chem. Soc. 2005, 127, 16046-16047
21. M. P. Cassidy, J. Raushel, V. V. Fokin, Angew. Chem. 2006, 118, 3226-3229
22. Angew. Chem. Int. Ed. 2006, 45, 3154-3157.
23. A. Brennführer, H. Neumann, M. Beller, Angew. Chem. 2009, 121, 4176-4196
24. Angew. Chem. Int. Ed. 2009, 48, 4114-4133
25. A. Schoenberg, R. F. Heck, J. Org. Chem. 1974, 39, 3327-3331
26. S. Ho, G. Bondarenko, D. Rosa, B. Dragisic, A. Orellana, J. Org. Chem. 2012, 77, 2008-2012
27. J. McNulty, J. J. Nair, A. Robertson, Org. Lett. 2007, 9, 4575-4578
28. J. R. Martinelli, D. A. Watson, D. M. M. Freckmann, T. E. Barder, S. L. Buchwald, J. Org. Chem. 2008, 73, 7102-7107
29. J. R. Martinelli, T. P. Clark, D. A. Watson, R. H. Munday, S. L. Buchwald, Angew. Chem. 2007, 119, 8612-8615
30. Angew. Chem. Int. Ed. 2007, 46, 8460-8463
31. W. Mägerlein, A. F. Indolese, M. Beller, Angew. Chem. 2001, 113, 2940-2943
32. Angew. Chem. Int. Ed. 2001, 40, 2856-2859.
33. K. Yamaguchi, M. Matsushita, N. Mizuno, Angew. Chem. 2004, 116, 1602-1606
34. Angew. Chem. Int. Ed. 2004, 43, 1576-1580
35. P. K. Mascharak, Coord. Chem. Rev. 2002, 225, 201-214
36. J. H. Kim, J. Britten, J. Chin, J. Am. Chem. Soc. 1993, 115, 3618-3622.
37. Y. Tamaru, Y. Yamada, Z. Yoshida, Synthesis 1983, 474-476
38. A. Tillack, I. Rudloff, M. Beller, Eur. J. Org. Chem. 2001, 523-528
39. J.-J. Shie, J.-M. Fang, J. Org. Chem. 2003, 68, 1158-1160
40. W.-J. Yoo, C. J. Li, J. Am. Chem. Soc. 2006, 128, 13064-13065
41. J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798-13799
42. J. Chan, K. D. Baucorn, J. A. Murry, J. Am. Chem. Soc. 2007, 129, 14106-14107
43. K. Ekoue-Kovi, C. Wolf, Org. Lett. 2007, 9, 3429-3432
44. L. Wang, H. Fu, Y. Y. Jiang, Y. F. Zhao, Chem. Eur. J. 2008, 14, 10722-10726
45. J. Gao, G. W. Wang, J. Org. Chem. 2008, 73, 2955-2958
46. K. R. Reddy, C. U. Maheswari, M. Venkateshwar, M. L. Kantam, Eur. J. Org. Chem. 2008, 3619-3622
47. L. Colombeau, T. Traore, P. Compain, O. R. Martin, J. Org. Chem. 2008, 73, 8647-8650
48. S. Seo, T. J. Marks, Org. Lett. 2008, 10, 317-319
49. C. Fang, W. X. Qian, W. L. Bao, Synlett 2008, 2529-2531
50. Y. Suto, N. Yamagiwa, Y. Torisawa, Tetrahedron Lett. 2008, 49, 5732-5735
51. J. M. Li, F. Xu, Y. Zhang, Q. Shen, J. Org. Chem. 2009, 74, 2575-2577
52. M. A. Ali, T. Punniyamurthy, Adv. Synth. Catal. 2010, 352, 288-292
53. C. L. Allen, S. Davulcu, J. M. J. Williams, Org. Lett. 2010, 12, 5096-5099
54. S. De Sarkar, A. Studer, Org. Lett. 2010, 12, 1992-1995
55. J. Liang, J. Lv, Z.-c. Shang, Tetrahedron 2011, 67, 8532-8535
56. S. C. Ghosh, J. S. Y. Ngiam, C. L. L. Chai, A. M. Seayad, T. T. Dang, A. Chen, Adv. Synth. Catal. 2012, 354, 1407-1412
57. K. S. Goh, C.-H. Tan, RSC Adv. 2012, 2, 5536-5538.
58. T. Naota, S. I. Murahashi, Synlett 1991, 693-694
59. C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790-792
60. L. U. Nordstrøm, H. Vogt, R. Madsen, J. Am. Chem. Soc. 2008, 130, 17672-17673
61. K. Shimizu, K. Ohshima, A. Satsuma, Chem. Eur. J. 2009, 15, 9977-9980
62. A. J. A. Watson, A. C. Maxwell, J. M. J. Williams, Org. Lett. 2009, 11, 2667-2670
63. T. Zweifel, J.-V. Naubron, H. Grützmacher, Angew. Chem. 2009, 121, 567-571
64. Angew. Chem. Int. Ed. 2009, 48, 559-563
65. S. C. Ghosh, S. Muthaiah, Y. Zhang, X. Y. Xu, S. H. Hong, Adv. Synth. Catal. 2009, 351, 2643-2649
66. S. Muthaiah, S. C. Ghosh, J. E. Jee, C. Chen, J. Zhang, S. H. Hong, J. Org. Chem. 2010, 75, 3002-3006
67. R. Ohmura, M. Takahata, H. Togo, Tetrahedron Lett. 2010, 51, 4378-4381
68. Y. Zhang, C. Chen, S. C. Ghosh, Y. Li, S. H. Hong, Organometallics 2010, 29, 1374-1378
69. C. Chen, S. H. Hong, Org. Biomol. Chem. 2011, 9, 20-26
70. J.-F. Soulé, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 18550-18553
71. Y. Wang, D. Zhu, L. Tang, S. Wang, Z. Wang, Angew. Chem. 2011, 123, 9079-9083
72. Angew. Chem. Int. Ed. 2011, 50, 8917-8921
73. S. Kegnæs, J. Mielby, U. V. Mentzel, T. Jensen, P. Fristrup, A. Riisager, Chem. Commun. 2012, 48, 2427-2429
74. J. Mielby, S. Kegnaes, P. Fristrup, ChemCatChem 2012, 4, 1037-1047
75. J.-F. Soulé, H. Miyamura, S. Kobayashi, Asian J. Org. Chem. 2012, 1, 319-321
76. K. Yamaguchi, H. Kobayashi, T. Oishi, N. Mizuno, Angew. Chem. 2012, 124, 559-562
77. Angew. Chem. Int. Ed. 2012, 51, 544-547
78. J. Zhu, Y. Zhang, F. Shi, Y. Deng, Tetrahedron Lett. 2012, 53, 3178-3180.
79. R. J. K. Taylor, M. Reid, J. Foot, S. A. Raw, Acc. Chem. Res. 2005, 38, 851-869.
80. M. Haruta, T. Kobayashi, H. Sano, N. Yamada, Chem. Lett. 1987, 16, 405-408
81. M. Haruta, N. Yamada, T. Kobayashi, S. Iijima, J. Catal. 1989, 115, 301-309
82. M. Haruta, Nature 2005, 437, 1098-1099
83. A. Corma, H. Garcia, Chem. Soc. Rev. 2008, 37, 2096-2126
84. T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037-3058
85. T. Tsukuda, H. Tsunoyama, H. Sakurai, Chem. Asian J. 2011, 6, 736-748
86. A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105
87. Angew. Chem. Int. Ed. 2006, 45, 7896-7936.
88. C. Della Pina, E. Falletta, L. Prati, M. Rossi, Chem. Soc. Rev. 2008, 37, 2077-2095
89. C. D. Pina, E. Falletta, M. Rossi, Chem. Soc. Rev. 2012, 41, 350-369
90. B. Guan, D. Xing, G. Cai, X. Wan, N. Yu, Z. Fang, L. Yang, Z. Shi, J. Am. Chem. Soc. 2005, 127, 18004-18005.
91. R. Akiyama, S. Kobayashi, Chem. Rev. 2009, 109, 594-642.
92. S. Kobayashi, H. Miyamura, Chem. Rec. 2010, 10, 271-290
93. S. Kobayashi, H. Miyamura, Aldrichimica Acta 2013, 46, 3-19.
94. H. Miyamura, R. Matsubara, Y. Miyazaki, S. Kobayashi, Angew. Chem. 2007, 119, 4229-4232
95. Angew. Chem. Int. Ed. 2007, 46, 4151-4154
96. C. Lucchesi, T. Inasaki, H. Miyamura, R. Matsubara, S. Kobayashi, Adv. Synth. Catal. 2008, 350, 1996-2000.
97. D. I. Enache, J. K. Edwards, P. Landon, B. Solsona-Espriu, A. F. Carley, A. A. Herzing, M. Watanabe, C. J. Kiely, D. W. Knight, G. J. Hutchings, Science 2006, 311, 362-365
98. S. Meenakshisundaram, E. Nowicka, P. J. Miedziak, G. L. Brett, R. L. Jenkins, N. Dimitratos, S. H. Taylor, D. W. Knight, D. Bethell, G. J. Hutchings, Faraday Discuss. 2010, 145, 341-356.
99. H. Miyamura, R. Matsubara, S. Kobayashi, Chem. Commun. 2008, 2031-2033.
100. K. Kaizuka, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2010, 132, 15096-15098.
101. S. K. Klitgaard, K. Egeblad, U. V. Mentzel, A. G. Popov, T. Jensen, E. Taarning, I. S. Nielsen, C. H. Christensen, Green Chem. 2008, 10, 419-423.
102. T. Ishida, M. Haruta, ChemSusChem 2009, 2, 538-541.
103. P. Preedasuriyachai, H. Kitahara, W. Chavasiri, H. Sakurai, Chem. Lett. 2010, 39, 1174-1176.
104. H. Miyamura, T. Yasukawa, S. Kobayashi, Green Chem. 2010, 12, 776-778
105. T. Yasukawa, H. Miyamura, S. Kobayashi, Chem. Asian J. 2011, 6, 621-627.
106. C. G. F. Siler, B. Xu, R. J. Madix, C. M. Friend, J. Am. Chem. Soc. 2012, 134, 12604-12610
107. L. Zhou, C. G. Freyschlag, B. J. Xu, C. M. Friend, R. J. Madix, Chem. Commun. 2010, 46, 704-706.
108. W.-J. Yoo, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 3095-3103.
109. J. He, I. Ichinose, T. Kunitake, A. Nakao, Y. Shiraishi, N. Toshima, J. Am. Chem. Soc. 2003, 125, 11034-11040.
110. J.-F. Soulé, H. Miyamura, S. Kobayashi, Chem. Commun. 2013, 49, 355-357.