Rhodium(III)-catalyzed ortho-arylation of anilides with aryl halides

Advanced Synthesis and Catalysis

Volumn 357, Issue 2-3, 2015, Pages 366-370

  Haridharan, Radhakrishnan ^a   Muralirajan, Krishnamoorthy ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

C c coupling; C h activation; Homogeneous catalysis; Iodobenzene; N phenylpivalamide; Rhodium

Indexed keywords

EID: 85027932458     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400798     Document Type: Article

References (90)

1. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651;
2. Modern Arylation Methods (Ed.: L. Ackermann), Wiley-VCH, Weinheim, 2009;
3. c) G. Bringmann, T. Gulder, T. A. M. Gulder, M. Breuning, Chem. Rev. 2011, 111, 563.
4. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976;
5. Angew. Chem. Int. Ed. 2009, 48, 9792
6. b) T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147;
7. c) O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074.
8. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407;
9. b) F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982;
10. c) A. S. Tsai, M. Brasse, R. G. Bergman, J. A. Ellman, Org. Lett. 2011, 13, 540;
11. d) N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7094;
12. e) J. Chen, G. Song, C.-L. Pan, X. Li, Org. Lett. 2010, 12, 5426;
13. f) S. Mochida, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 3024;
14. g) X. Li, M. Zhao, J. Org. Chem. 2011, 76, 8530;
15. h) S. H. Park, J. Y. Kim, S. Chang, Org. Lett. 2011, 13, 2372;
16. F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096
17. Angew. Chem. Int. Ed. 2011, 50, 1064;
18. j) H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, Z.-J. Shi, J. Am. Chem. Soc. 2011, 133, 15244.
19. M. P. Huestis, L. Chan, D. R. Stuart, K. Fagnou, Angew. Chem. 2011, 123, 1374
20. ; Angew. Chem. Int. Ed. 2011, 50, 1338;
21. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2011, 123, 4255
22. Angew. Chem. Int. Ed. 2011, 50, 4169
23. J. Jayakumar, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2012, 124, 201
24. ; Angew. Chem. Int. Ed. 2012, 51, 197;
25. d) C.-Z. Luo, P. Gandeepan, J. Jayakumar, K. Parthasarathy, Y.-W. Chang, C.-H. Cheng, Chem. Eur. J. 2013, 19, 14181;
26. W. Dong, L. Wang, K. Parthasarathy, F. Pan, C. Bolm, Angew. Chem. 2013, 125, 11787
27. ; Angew. Chem. Int. Ed. 2013, 52, 11573
28. f) S.-C. Chuang, P. Gandeepan, C.-H. Cheng, Org. Lett. 2013, 15, 5750;
29. N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem. 2008, 120, 4083
30. ; Angew. Chem. Int. Ed. 2008, 47, 4019
31. h) S. Mochida, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Lett. 2010, 39, 744;
32. i) P. C. Too, Y.-F. Wang, S. Chiba, Org. Lett. 2010, 12, 5688;
33. j) T. K. Hyster, T. Rovis, J. Am. Chem. Soc. 2010, 132, 10565;
34. k) S. Rakshit, F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9585;
35. l) N. Umeda, K. Hirano, T. Satoh, N. Shibata, H. Sato, M. Miura, J. Org. Chem. 2011, 76, 13;
36. m) N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449;
37. n) F. W. Patureau, T. Besset, N. Kuhl, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2154;
38. o) T. K. Hyster, T. Rovis, Chem. Commun. 2011, 47, 11846;
39. B.-J. Li, H.-Y. Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem. 2012, 124, 4014
40. ; Angew. Chem. Int. Ed. 2012, 51, 3948;
41. q) C.-Z. Luo, P. Gandeepan, C.-H. Cheng, Chem. Commun. 2013, 49,8528.
42. a) A. S. Tsai, M. E. Tauchert, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 1248;
43. Y. Li, B.-J. Li, W.-H. Wang, W.-P. Huang, X.-S. Zhang, K. Chen, Z.-J. Shi, Angew. Chem. 2011, 123, 2163
44. ; Angew. Chem. Int. Ed. 2011, 50, 2115.
45. K. Chen, H. Li, Y. Li, X.-S. Zhang, Z.-Q. Lei, Z.-J. Shi, Chem. Sci. 2012, 3, 1645;
46. J. Wencel-Delord, C. Nimphius, F. W. Patureau, F. Glorius, Angew. Chem. 2012, 124, 2290
47. ; Angew. Chem. Int. Ed. 2012, 51, 2247;
48. J. Dong, Z. Long, F. Song, N. Wu, Q. Guo, J. Lan, J. You, Angew. Chem. 2013, 52, 580
49. ; Angew. Chem. Int. Ed. 2013, 52, 580
50. d) R. K. Chinnagolla, M. Jeganmohan, Org. Lett. 2012, 14, 5246;
51. e) R. K. Chinnagolla, M. Jeganmohan, Chem. Commun. 2014, 50, 2442;
52. f) T. Pirali, F. Zhang, A. H. Miller, J. L. Head, D. McAusland, M. F. Greaney, Angew. Chem. Int. Ed. 2012, 51, 1006;
53. g) T. Truong, O. Daugulis, Org. Lett. 2012, 14, 5964;
54. h) X. Zhang, F. Wang, Z. Qi, S. Yu, X. Li, Org. Lett. 2014, 16, 1586.
55. a) J. Karthikeyan, R. Haridharan, C.-H. Cheng, Angew. Chem. Int. Ed. 2012, 51, 12343;
56. b) N. Senthilkumar, K. Parthasarathy, P. Gandeepan, C.-H. Cheng, Chem. Asian J. 2013, 8, 2175;
57. c) J. Kwak, M. Kim, S. Chang, J. Am. Chem. Soc. 2011, 133, 3780;
58. d) M.-Z. Lu, P. Lu, Y.-H. Xu, T.-P. Loh, Org. Lett. 2014, 16, 2614.
59. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
60. Angew. Chem. Int. Ed. 2009, 48, 5094;
61. b) C.-J. Li, Acc. Chem. Res. 2009, 42, 335;
62. c) F. Kakiuchi, T. Kochi, Synthesis 2008, 3013.
63. a) S. J. Tremont, H. ur Rahman, J. Am. Chem. Soc. 1984, 106, 5759;
64. b) D. Shabashov, O. Daugulis, J. Org. Chem. 2007, 72, 7720;
65. V. G. Zaitsev, O. Daugulis, Angew. Chem. 2005, 117, 4114
66. ; Angew. Chem. Int. Ed. 2005, 44, 4046
67. d) G. Brasche, J. Garcia-Fortanet, S. L. Buchwald, Org. Lett. 2008, 10, 2207;
68. e) J. J. Mousseau, F. Vallee, M. M. Lorion, A. B. Charette, J. Am. Chem. Soc. 2010, 132, 14412;
69. f) C. S. Yeung, X. Zhao, N. Borduas, V. M. Dong, Chem. Sci. 2010, 1, 331;
70. g) D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330;
71. h) S. Yang, B. Li, X. Wan, Z.-J. Shi, J. Am. Chem. Soc. 2007, 129, 6066;
72. i) F. Yang, F. Song, W. Li, J. Lan, J. You, RSC Advances 2013, 3, 9649.
73. a) K. Parthasarathy, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2008, 10, 325;
74. V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2008, 120, 9604
75. ; Angew. Chem. Int. Ed. 2008, 47, 9462;
76. c) V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Chem. Eur. J. 2010, 16, 1436;
77. d) P. Gandeepan, K. Parthasarathy, C.-H. Cheng, J. Am. Chem. Soc. 2010, 132, 8569;
78. J. Karthikeyan, C.-H. Cheng, Angew. Chem. 2011, 123, 10054
79. Angew. Chem. Int. Ed. 2011, 50, 9880;
80. f) K. Muralirajan, C.-H. Cheng, Chem. Eur. J. 2013, 19, 6198.
81. 3 and 4 equiv of iodobenzene, 25% of 2,6-diarylated product was also observed in addition to the mono-arylated product 3a (63%).
82. D. R. Stuart, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326.
83. a) N. Schroder, J. Wencel-Delord, F. Glorius, J. Am. Chem. Soc. 2012, 134, 8298;
84. b) J. Ryu, K. Shin, S. H. Park, J. Y. Kim, S. Chang, Angew. Chem. Int. Ed. 2012, 51, 9904.
85. E. H. Simmons, J. F. Hartwig, Angew. Chem. 2012, 124, 3120
86. Angew. Chem. Int. Ed. 2012, 51, 3066
87. b) P. Gandeepan, C.-H. Cheng, J. Am. Chem. Soc. 2012, 134, 5738;
88. c) C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1999, 121, 6616.
89. a) J. Xi, Q.-L. Dong, G.-S. Liu, S. Wang, L. Chen, Z.-J. Yao, Synlett 2010, 11, 1674;
90. b) K. Hattori, H. Yamamoto, A. Iwashita, K. Mihara, N. Matsuoka, J. Ishita, Bioorg. Med. Chem. Lett. 2005, 15, 4221.