Practical synthesis of amides from alkynyl bromides, amines, and water

Tetrahedron

Volumn 67, Issue 33, 2011, Pages 5920-5927

  Chen, Zheng Wang ^a,b   Jiang, Huan Feng ^a   Pan, Xiao Yan ^a   He, Zai Jun ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b Gannan Teachers' College   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 (INDOLIN 1 YL) 2 PHENYLETHANONE; 1 MORPHOLINO 2 PHENYLETHANONE; 2 (3 CHLOROPHENYL) 1 MORPHOLINOETHANONE; 2 (3 FLUOROPHENYL) 1 MORPHOLINOETHANONE; 2 (4 BROMOPHENYL) N,N DIETHYLACETAMIDE; 2 (4 TERT BUTYLPHENYL) N,N DIETHYLACETAMIDE; 2 PHENYL 1 (PYRROLIDIN 1 YL) ETHANONE; 2 PHENYL 1 THIOMORPHOLINOETHANONE; 2 PHENYL N,N DIPROPYLACETAMIDE; 2- [2 (TRIFLUOROMETHYL)PHENYL] 1 MORPHOLINOETHANONE; ALKYNYL GROUP; AMIDE; AMINE; BROMINE DERIVATIVE; N BENZYL 2 PHENYLACETAMIDE; N BUTYL 2 PHENYLACETAMIDE; N CYCLOHEXYL 2 PHENYLACETAMIDE; N SEC BUTYL 2 PHENYLACETAMIDE; N,N DIALLYL 2 PHENYLACETAMIDE; N,N DIBENZYL 2 PHENYLACETAMIDE; N,N DIETHYL 2 (2 FLUOROPHENYL) ACETAMIDE; N,N DIETHYL 2 (3 FLUOROPHENYL) ACETAMIDE; N,N DIETHYL 2 (4 BIPHENYL) ACETAMIDE; N,N DIETHYL 2 (4 FLUOROPHENYL) ACETAMIDE; N,N DIETHYL 2 (4 METHOXYPHENYL) ACETAMIDE; N,N DIETHYL 2 PHENYLACETAMIDE; N,N DIETHYL 2 TOLYLACETAMIDE; N,N DIISOPROPYL 2 PHENYLACETAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; ENERGY YIELD; METHODOLOGY; PRIORITY JOURNAL; SYNTHESIS;

EID: 79960251359     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.06.045     Document Type: Article

References (59)

1. J.M. Humphrey, and A.R. Chamberlin Chem. Rev. 97 1997 2243
2. J.S. Carey, D. Laffan, C. Thomson, and M.T. Williams Org. Biomol. Chem. 4 2006 2337
3. J.-M. Gaudin, T. Lander, and O. Nikolaenko Chem. Biodiversity 5 2008 617
4. A.K. Ghose, V.N. Viswanadhan, and J.J. Wendoloski J. Comb. Chem. 1 1999 55
5. D.J.C. Constable, P.J. Dunn, J.D. Hayler, G.R. Humphrey, J.L. Leazer, R.J. Linderman, K. Lorenz, J. Manley, B.A. Pearlman, A. Wells, A. Zaks, and T.Y. Zhang Green Chem. 9 2007 411
6. E. Valeur, and M. Bradley Chem. Soc. Rev. 38 2009 606
7. R.M. Al-Zoubi, O. Marion, and D.G. Hall Angew. Chem., Int. Ed. 47 2008 2876
8. J.W. Comerford, J.H. Clark, D.J. Macquarrie, and S.W. Breeden Chem. Commun. 2009 2562
9. A.R. Katritzky, C. Cai, and S.K. Singh J. Org. Chem. 71 2006 3375
10. G.A. Molander, J. Raushel, and N.M. Ellis J. Org. Chem. 75 2010 4304
11. A. Teichert, K. Jantos, K. Harms, and A. Studer Org. Lett. 6 2004 3477
12. D.M. Shendage, R. Fröhlich, and G. Haufe Org. Lett. 6 2004 3675
13. D.A. Black, and B.A. Arndtsen Org. Lett. 8 2006 1991
14. I. Azumaya, T. Okamoto, F. Imabeppu, and H. Takayanagi Tetrahedron 59 2003 2325
15. E. Saxon, and C.R. Bertozzi Science 287 2000 2007
16. F. Damkaci, and P. DeShong J. Am. Chem. Soc. 125 2003 4408
17. N. Shangguan, S. Katukojvala, R. Greenberg, and L.J. Williams J. Am. Chem. Soc. 125 2003 7754
18. B.L. Nilsson, L.L. Kiessling, and R.T. Raines Org. Lett. 2 2000 1939
19. R. Merkx, A.J. Brouwer, D.T.S. Rijkers, and R.M.J. Liskamp Org. Lett. 7 2005 1125
20. L. Yao, and J. Aubé J. Am. Chem. Soc. 129 2007 2766
21. Y.-S. Lin, and H. Alper Angew. Chem., Int. Ed. 40 2001 779
22. Y. Uozumi, T. Arii, and T. Watanabe J. Org. Chem. 66 2001 5272
23. P. Nanayakkara, and H. Alper Chem. Commun. 2003 2384
24. A. Schoenberg, and R.F. Heck J. Org. Chem. 39 1974 3327
25. S.I. Lee, S.U. Son, and Y.K. Chung Chem. Commun. 2002 1310
26. Y. Uenoyama, T. Fukuyama, O. Nobuta, H. Matsubara, and I. Ryu Angew. Chem., Int. Ed. 44 2005 1075
27. D.J. Knapton, and T.Y. Meyer Org. Lett. 6 2004 687
28. C. Gunanathan, Y. Ben-David, and D. Milstein Science 317 2007 790
29. S.C. Ghosh, S. Muthaiah, Y. Zhang, X. Xu, and S.H. Hong Adv. Synth. Catal. 351 2009 2643
30. N.A. Owston, A.J. Parker, and J.M.J. Williams Org. Lett. 9 2007 73
31. W.-J. Yoo, and C.-J. Li J. Am. Chem. Soc. 128 2006 13064
32. J. Chan, K.D. Baucom, and J.A. Murry J. Am. Chem. Soc. 129 2007 14106
33. H.U. Vora, and T. Rovis J. Am. Chem. Soc. 129 2007 13796
34. J.W. Bode, and S.S. Sohn J. Am. Chem. Soc. 129 2007 13798
35. J. Li, F. Xu, Y. Zhang, and Q. Shen J. Org. Chem. 74 2009 2575
36. K. Ishihara, and T. Yano Org. Lett. 6 2004 1983
37. S. Seo, and T.J. Marks Org. Lett. 10 2008 317
38. K. Ekoue-Kovi, and C. Wolf Org. Lett. 9 2007 3429
39. H. Fujiwara, Y. Ogasawara, K. Yamaguchi, and N. Mizuno Angew. Chem., Int. Ed. 46 2007 5202
40. C. Ramalingan, and Y.-T. Park J. Org. Chem. 72 2007 4536
41. R.S. Ramón, J. Bosson, S. Díez-González, N. Marion, and S.P. Nolan J. Org. Chem. 75 2010 1197
42. N.A. Owston, A.J. Parker, and J.M. Williams J. Org. Lett. 9 2007 3599
43. B. Shen, D.M. Makley, and J.N. Johnston Nature 465 2010 1027
44. H. Jiang, B. Liu, Y. Li, A. Wang, and H. Huang Org. Lett. 13 2011 1028
45. W.-K. Chan, C.-M. Ho, M.-K. Wong, and C.-M. Che J. Am. Chem. Soc. 128 2006 14796
46. M.P. Cassidy, J. Raushel, and V.V. Fokin Angew. Chem., Int. Ed. 45 2006 3154
47. S.H. Cho, E.J. Yoo, I. Bae, and S. Chang J. Am. Chem. Soc. 127 2005 16046
48. M.O. Frederick, J.A. Mulder, M.R. Tracey, R.P. Hsung, J. Huang, K.C.M. Kurtz, L. Shen, and C.J. Douglas J. Am. Chem. Soc. 125 2003 2368
49. C. Laroche, J. Li, M.W. Freyer, and S.M. Kerwin J. Org. Chem. 73 2008 6462
50. K. Dooleweerdt, H. Birkedal, T. Ruhland, and T. Skrydstrup J. Org. Chem. 73 2008 9447
51. B. Yao, Z. Liang, T. Niu, and Y. Zhang J. Org. Chem. 74 2009 4630
52. J.R. Dunetz, and R.L. Danheiser Org. Lett. 5 2003 4011
53. Y. Zhang, R.P. Hsung, M.R. Tracey, C.M. Kimberly, K.C.M. Kurtz, and E.L. Vera Org. Lett. 6 2004 1151
54. Y. Li, X. Liu, H. Jiang, and Z. Feng Angew. Chem., Int. Ed. 49 2010 3338
55. Z. Chen, J. Li, H. Jiang, S. Zhu, Y. Li, and C. Qi Org. Lett. 12 2010 3262
56. Z. Chen, H. Jiang, Y. Li, and C. Qi Chem. Commun. 46 2010 8049
57. C. Zhang, and N. Jiao J. Am. Chem. Soc. 132 2010 28
58. S.R. Sandler, and W. Karo Organic Functional Group Preparations Vol. 2 1983 Academic San Diego 135 151
59. K.I. Booker-Milburn A.R. Katritzky, O. Meth-Cohn, C.W. Rees, Comprehensive Organic Functional Group Transformations Vol. 2 1995 Pergamon Oxford 1039 1058