Organocatalytic amidation and esterification of aldehydes with activating reagents by a cross-coupling strategy

Angewandte Chemie - International Edition

Volumn 51, Issue 50, 2012, Pages 12538-12541

  Tan, Bin ^a   Toda, Narihiro ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

aldehydes; cross coupling; N hydroxyimides; organocatalysis; sulfonimides

Indexed keywords

ACTIVATING REAGENTS; AMIDATION; BROAD APPLICATION; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; HEXAFLUOROISOPROPYL ALCOHOLS; N-HYDROXYIMIDES; ONE POT; ORGANOCATALYSIS; ORGANOCATALYTIC; SIMPLE METHOD; SULFONIMIDES; SYNTHESIS OF AMIDE;

ALDEHYDES; AMIDES; ESTERS; REACTION KINETICS;

ESTERIFICATION;

ALCOHOL DERIVATIVE; ALDEHYDE; AMIDE; ESTER; IMIDE;

ARTICLE; CATALYSIS; CHEMISTRY; ESTERIFICATION;

ALCOHOLS; ALDEHYDES; AMIDES; CATALYSIS; ESTERIFICATION; ESTERS; IMIDES;

EID: 84870615882     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201205921     Document Type: Article

References (67)

1. M. J. Humphrey, R. A. Chamberlin, Chem. Rev. 1997, 97, 2243
2. C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405
3. R. M. Wilson, J. L. Stockdill, X. Wu, X. Li, P. A. Vadola, P. K. Park, P. Wang, S. J. Danishefsky, Angew. Chem. 2012, 124, 2888
4. Angew. Chem. Int. Ed. 2012, 51, 2834.
5. C. A. G. N. Montalbetti, V. Falque, Tetrahedron 2005, 61, 10827
6. E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606
7. V. R. Pattabiraman, J. W. Bode, Nature 2012, 480, 471.
8. G. H. L. Nefkens, G. I. Tesser, J. Am. Chem. Soc. 1961, 83, 1263
9. G. W. Anderson, J. E. Zimmerman, F. M. Callahan, J. Am. Chem. Soc. 1964, 86, 1839
10. G. W. Cline, S. B. Hanna, J. Am. Chem. Soc. 1987, 109, 3087
11. M. Bodanzsky, Principles of Peptide Synthesis 2 nd ed., Springer, New York, 1993.
12. E. Grochowski, J. Jurczak, Synthesis 1977, 277
13. H. Ogura, T. Kobayashi, K. Shimizu, K. Kawabe, K. Takeda, Tetrahedron Lett. 1979, 20, 4745
14. S. Kim, K. Y. Ko, J. Chem. Soc. Chem. Commun. 1985, 473
15. P. Pöchlauer, W. Hendel, Tetrahedron 1998, 54, 3489
16. M. Kim, K. J. Han, Synth. Commun. 2009, 39, 4467.
17. 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, T. Y. Zhang, Green Chem. 2007, 9, 411.
18. K. Ekoue-Kovi, C. Wolf, Chem. Eur. J. 2008, 14, 6302.
19. W. Yoo, C. Li, J. Am. Chem. Soc. 2006, 128, 13064
20. K. Ekoue-Kovi, C. Wolf, Org. Lett. 2007, 9, 3429
21. K. Reddy, C. U. Maheswari, M. Venkateshwar, M. L. Kantam, Eur. J. Org. Chem. 2008, 3619
22. S. Y. Seo, T. J. Marks, Org. Lett. 2008, 10, 317
23. J. Li, F. Xu, Y. Zhang, Q. Shen, J. Org. Chem. 2009, 74, 2575
24. C. L. Allen, S. Davulcu, J. M. J. Williams, Org. Lett. 2010, 12, 5096
25. C. Zhang, Z. Xu, L. Zhang, N. Jiao, Angew. Chem. 2011, 123, 11284
26. Angew. Chem. Int. Ed. 2011, 50, 11088
27. C. Zhang, X. Zong, L. Zhang, N. Jiao, Org. Lett. 2012, 14, 3280
28. 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.
29. V. V. Zhdankin, Chem. Rev. 2008, 108, 5299
30. C. Fang, W, Qian, W. Bao, Synlett 2008, 2529
31. V. Prasad, R. R. Kale, B. B. Mishra, D. Kumar, V. K. Tiwari, Org. Lett. 2012, 14, 2936.
32. Z. Liu, J. Zhang, S. Chen, E. Shi, Y. Xu, X. Wan, Angew. Chem. 2012, 124, 3285
33. Angew. Chem. Int. Ed. 2012, 51, 3231.
34. M. Uyanik, H. Okamoto, T. Yasui, K. Ishihara, Science 2010, 328, 1376; for other reports, see
35. M. Uyanik, D. Suzuki, T. Yasui, K. Ishihara, Angew. Chem. 2011, 123, 5443
36. Angew. Chem. Int. Ed. 2011, 50, 5331
37. T. Froehr, C. P. Sindlinger, U. Kloeckner, P. Finkbeiner, B. J. Nachtsheim, Org. Lett. 2011, 13, 3754
38. S. Chen, Y. Xu, X. Wan, Org. Lett. 2011, 13, 6152
39. L. Chen, E. Shi, Z. Liu, S. Chen, W. Wei, H. Li, K. Xu, X. Wan, Chem. Eur. J. 2011, 17, 4085
40. W. Wei, C. Zhang, Y. Xu, X. Wan, Chem. Commun. 2011, 47, 10827
41. L. Ma, X. Wang, W. Yu, B. Han, Chem. Commun. 2011, 47, 11333
42. J. Xie, H. Jiang, Y. Cheng, C. Zhu, Chem. Commun. 2012, 48, 979
43. J. Feng, S. Liang, S. Chen, J. Zhang, S. Fu, X. Yu, Adv. Synth. Catal. 2012, 354, 1287.
44. K. Y. K. Chow, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 8126
45. N. Y. Reynolds, J. R. deAlaniz, T. Rovis, J. Am. Chem. Soc. 2004, 126, 9518
46. R. M. Al-Zoubi, O. Marion, D. G. Hall, Angew. Chem. 2008, 120, 2918
47. Angew. Chem. Int. Ed. 2008, 47, 2876
48. J. Guin, S. D. Sarkar, S. Grimme, A. Studer, Angew. Chem. 2008, 120, 8855
49. Angew. Chem. Int. Ed. 2008, 47, 8727
50. S. D. Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc. 2010, 132, 1190
51. S. Kuwano, S. Harada, R. Oriez, K. Yamada, Chem. Commun. 2012, 48, 145
52. C. L. Allen, B. N. Atkinson, J. M. J. Williams, Angew. Chem. 2012, 124, 1412
53. Angew. Chem. Int. Ed. 2012, 51, 1383
54. T. B. Nguyen, J. Sorres, M. Q. Tran, L. Ermolenko, A. Al-Mourabit, Org. Lett. 2012, 14, 3202
55. Y. Zhao, Y. Tam, Y. Wang, Z. Li, J. Sun, Org. Lett. 2012, 14, 1398
56. M. Feroci, I. Chiarotto, M. Orsini, R. Pelagalli, A. Inesi, Chem. Commun. 2012, 48, 5361
57. E. E. Finney, K. A. Ogawa, A. J. Boydston, J. Am. Chem. Soc. 2012, 134, 12374.
58. During the preparation of this manuscript, a related transformation catalyzed by cobalt was reported; see:, H. Yao, K. Yamamoto, Chem. Asian J. 2012, 7, 1542; see also Ref. [17].
59. 4NBr acted as a bromination reagent:, T. Nagano, Z. Jia, X. Li, G. Liu, A. S. C. Chan, T. Hayashi, Chem. Lett. 2010, 39, 929.
60. E. G. Klauber, C. K. De, T. K. Shah, D. Seidel, J. Am. Chem. Soc. 2010, 132, 13624
61. C. K. De, D. Seidel, J. Am. Chem. Soc. 2011, 133, 14538
62. C. K. De, N. Mittal, D. Seidel, J. Am. Chem. Soc. 2011, 133, 16802.
63. A. Nakano, K. Takahashi, J. Ishihara, S. Hatakeyama, Org. Lett. 2006, 8, 5357
64. S. M. Sarkar, E. N. Wanzala, S. Shibahara, K. Takahashi, J. Ishihara, S. Hatakeyama, Chem. Commun. 2009, 5907
65. S. De Sarkar, A. Studer, Org. Lett. 2010, 12, 1992.
66. M. Rueda-Becerril, C. C. Sazepin, J. C. T. Leung, T. Okbinoglu, P. Kennepohl, J. F. Paquin, G. M. Sammis, J. Am. Chem. Soc. 2012, 134, 4026.
67. H. Yao, Y. Tung, K. Yamamoto, Tetrahedron Lett. 2012, 53, 5094.