Palladium-catalyzed direct C-H arylation of enamides with simple arenes

Angewandte Chemie - International Edition

Volumn 51, Issue 23, 2012, Pages 5701-5705

  Pankajakshan, Sreekumar ^b   Xu, Yun He ^a   Cheng, Jun Kee ^b   Low, Man Ting ^b   Loh, Teck Peng ^a,b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b Nanyang Technological University   (Singapore)

Author keywords

arylation; C H functionalization; enamides; palladium; synthetic methods

Indexed keywords

ARYLATIONS; C-H ARYLATION; C-H FUNCTIONALIZATION; ENAMIDES; MOLECULAR COMPLEXITY; MONOARYLATION; PALLADIUM-CATALYZED; SYNTHETIC METHODS; SYNTHETIC ROUTES;

CATALYSIS; PALLADIUM;

AROMATIC COMPOUNDS;

EID: 84861625900     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201109247     Document Type: Article

References (74)

1. nd Completely Revised and Enlarged ed., (Eds.: A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004
2. Metal-Catalyzed Cross-Coupling Reactions, Vol. 1, 2nd Completely Revised and Enlarged ed., (Eds.: A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004
3. Metal-Catalyzed Cross-Coupling Reactions (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, Weinhein, 1998.
4. G. Dyker, Angew. Chem. 1999, 111, 1808
5. Angew. Chem. Int. Ed. 1999, 38, 1698
6. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
7. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
8. B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949
9. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
10. ngew. Chem. Int. Ed. 2009, 48, 5094
11. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
12. Angew. Chem. Int. Ed. 2009, 48, 9792
13. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242
14. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
15. L.-M. Xu, Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712
16. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677.
17. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
18. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068.
19. 3 C-H arylation in total synthesis, see:, W. R. Gutekunst, P. S. Baran, J. Am. Chem. Soc. 2011, 133, 19076.
20. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586
21. G. Cai, Y. Fu, Y. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 7666
22. J.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. 2008, 120, 6552
23. Angew. Chem. Int. Ed. 2008, 47, 6452
24. S. Würtz, S. Rakshit, J. Neumann, T. Dröge, F. Glorius, Angew. Chem. 2008, 120, 7340
25. Angew. Chem. Int. Ed. 2008, 47, 7230
26. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254
27. C. E. Houlden, C. D. Bailey, J. G. Ford, M. R. Gagne, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2008, 130, 10066
28. A. García-Rubia, R. G. Arrays, J. C. Carretero, Angew. Chem. 2009, 121, 6633
29. Angew. Chem. Int. Ed. 2009, 48, 6511
30. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072
31. D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315
32. J. A. Schiffner, T. H. Wöste, M. Oestreich, Eur. J. Org. Chem. 2010, 174
33. Y. Lu, D.-H. Wang, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916
34. X. G. Zhang, S. L. Fan, C. Y. He, X. L. Wan, Q. Q. Min, J. Yang, Z. X. Jiang, J. Am. Chem. Soc. 2010, 132, 4506
35. M. C. Ye, G. L. Gao, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 6964.
36. For the first report, see:, I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119.
37. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633
38. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107
39. The Mizoroki-Heck Reaction, (Ed.:, M. Oestreich,), Wiley, Hoboken, 2009.
40. D. R. Carbery, Org. Biomol. Chem. 2008, 6, 3455; recently our group has reported the aliphatic C-H oxidation of amines and aldehydes through enamine intermediates. see
41. J.-S. Tian, T. P. Loh, Angew. Chem. 2010, 122, 8595
42. Angew. Chem. Int. Ed. 2010, 49, 8417
43. J.-S. Tian, T. P. Loh, Chem. Commun. 2011, 47, 5458.
44. W. Cabri, I. Candiani, A. Bedeschi, R. Santi, J. Org. Chem. 1993, 58, 7421
45. M. M. S. Andappan, P. Nilsson, H. von Schenck, M. Larhed, J. Org. Chem. 2004, 69, 5212
46. P. Harrison, G. Meek, Tetrahedron Lett. 2004, 45, 9277
47. J. Mo, L. J. Xu, J. L. Xiao, J. Am. Chem. Soc. 2005, 127, 751
48. A. L. Hansen, T. Skrydstrup, J. Org. Chem. 2005, 70, 5997
49. J. Mo, J. L. Xiao, Angew. Chem. 2006, 118, 4258
50. Angew. Chem. Int. Ed. 2006, 45, 4152
51. Z. Hyder, J. W. Ruan, J. L. Xiao, Chem. Eur. J. 2008, 14, 5555
52. Z. Liu, D. Xu, W. Tang, L. Xu, J. Mo, J. L. Xiao, Tetrahedron Lett. 2008, 49, 2756
53. Y. Liu, D. Li, C. M. Park, Angew. Chem. 2011, 123, 7471
54. Angew. Chem. Int. Ed. 2011, 50, 7333.
55. H. Zhou, W. J. Chung, Y. H. Xu, T. P. Loh, Chem. Commun. 2009, 3472
56. H. Zhou, Y. H. Xu, W. J. Chung, T. P. Loh, Angew. Chem. 2009, 121, 5459
57. Angew. Chem. Int. Ed. 2009, 48, 5355; For isolation and characterization of the palladacycle from enamide, see
58. Y. H. Xu, Y. K. Chok, T. P. Loh, Chem. Sci. 2011, 2, 1822.
59. Chiral Amine Synthesis: Methods, Developments and Applications (Ed.:, C. T. Nugent,), Wiley-VCH, Weinheim, 2010
60. A. B. Flynn, W. W. Ogilvie, Chem. Rev. 2007, 107, 4698.
61. For a discussion on these selectivity issues and a hydrogen-bond-directed synthesis of Z-enamides, see:, J. M. Lee, D.-S Ahn, D. Y. Jung, J. Lee, Y. Do, S. K. Kim, S. Chang, J. Am. Chem. Soc. 2006, 128, 12954.
62. For a report on palladium-catalyzed arylation of indoles, see:, D. R. Stuart, K. Fagnou, Science 2007, 316, 1172
63. The addition of indole to a Boc-protected enamide was reported using a stoichiometric amount of palladium acetate. see:, Y. Yokoyama, T. Matsumoto, Y. Murakami, J. Org. Chem. 1995, 60, 1486.
64. Y. Fujiwara, I. Moritani, S. Danno, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166
65. R. Asano, I. Moritani, Y. Fujiwara, S. Teranishi, Chem. Commun. 1970, 1293
66. Y. Fujiwara, R. Asano, I. Moritani, S. Teranishi, J. Org. Chem. 1976, 41, 1681
67. Y. Fujiwara, K. Takaki, Y. Taniguchi, Synlett 1996, 591
68. Y. Fuchita, K. Hiraki, Y. Kamogawa, M. Suenaga, K. Toggoh, Y. Fujiwara, Bull. Chem. Soc. Jpn. 1989, 62, 1081
69. W. Lu, Y. Yamaoka, Y. Taniguchi, T. Kitamura, Y. Fujiwara, J. Organomet. Chem. 1999, 580, 290
70. C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097
71. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992
72. C. G. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am. Chem. Soc. 2000, 122, 7252.
73. The Fujiwara-Moritani reaction was shown to exhibit a primary KIE. See:, P. Müller, E. Katten, J. Roček, J. Am. Chem. Soc. 1971, 93, 7116.
74. For a review on palladacycles, see:, J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527.