Asymmetric organocatalytic direct C(sp2)-H/C(sp3)-H oxidative cross-coupling by chiral iodine reagents

Angewandte Chemie - International Edition

Volumn 53, Issue 13, 2014, Pages 3466-3469

  Wu, Hua ^a   He, Yu Ping ^a   Xu, Lue ^a   Zhang, Dong Yang ^a   Gong, Liu Zhu ^a  

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

Author keywords

asymmetric catalysis; C H functionalization; chirality; cross coupling; organoiodine

Indexed keywords

CATALYSTS; CHIRALITY; ENANTIOSELECTIVITY; IODINE COMPOUNDS;

ALTERNATIVE CATALYSTS; ASYMMETRIC CATALYSIS; C-H FUNCTIONALIZATION; CROSS-COUPLINGS; ENANTIOSELECTIVE; FUNCTIONALIZATIONS; ORGANOIODINE; OXIDATIVE COUPLING REACTIONS;

CHEMICAL REACTIONS;

EID: 84896463710     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309967     Document Type: Article

References (67)

1. G. P. McGlacken, L. M. Bateman, Chem. Soc. Rev. 2009, 38, 2447-2464
2. J. A. Ashenhurst, Chem. Soc. Rev. 2010, 39, 540-548
3. X. Bugaut, F. Glorious, Angew. Chem. 2011, 123, 7618-7620
4. Angew. Chem. Int. Ed. 2011, 50, 7479-7481
5. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorious, Angew. Chem. 2012, 124, 10382-10401
6. Angew. Chem. Int. Ed. 2012, 51, 10236-10254.
7. J. Yu, R. Giri, X. Chen, Org. Biomol. Chem. 2006, 4, 4041-4047
8. R. Giri, B. Shi, K. M. Engle, N. Maugel, J. Yu, Chem. Soc. Rev. 2009, 38, 3242-3272
9. C. Li, Acc. Chem. Res. 2009, 42, 335-344
10. X. Chen, K. M. Engle, D. Wang, J. Yu, Angew. Chem. 2009, 121, 5196-5217
11. Angew. Chem. Int. Ed. 2009, 48, 5094-5115
12. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215-1292
13. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780-1824
14. K. M. Engle, T. Mei, M. Wasa, J. Yu, Acc. Chem. Res. 2012, 45, 788-802.
15. B. Shi, Y. Zhang, J. K. Lam, D. Wang, J. Yu, J. Am. Chem. Soc. 2010, 132, 460-461
16. C. Guo, J. Song, L. Gong, Angew. Chem. 2010, 122, 5690-5694
17. Angew. Chem. Int. Ed. 2010, 49, 5558-5562
18. H. Egami, K. Matsumoto, T. Oguma, T. Kunisu, T. Katsuki, J. Am. Chem. Soc. 2010, 132, 13633-13635
19. M. Wasa, K. M. Engle, D. W. Lin, E. J. Yoo, J. Yu, J. Am. Chem. Soc. 2011, 133, 19598-19601
20. D. Gao, Y. Shi, Q. Gu, Z. Zhao, S. You, J. Am. Chem. Soc. 2013, 135, 86-89
21. X. Cheng, Y. Li, Y. Su, F. Yin, J. Wang, J. Sheng, H. U. Vora, X. Wang, J. Yu, J. Am. Chem. Soc. 2013, 135, 1236-1239
22. B. M. Trost, D. A. Thaisrivongs, E. J. Donckele, Angew. Chem. 2013, 125, 1563-1566
23. Angew. Chem. Int. Ed. 2013, 52, 1523-1526
24. G. Chen, K. Chen, Z. Shi, ChemCatChem 2013, 5, 1289-1290.
25. Y. K. Kang, S. M. Kim, D. Y. Kim, J. Am. Chem. Soc. 2010, 132, 11847-11849
26. K. Mori, S. Sueoka, T. Akiyama, J. Am. Chem. Soc. 2011, 133, 2424-2426
27. Y. He, Y. Du, S. Luo, L. Gong, Tetrahedron Lett. 2011, 52, 7064-7066
28. Z. Jiao, S. Zhang, C. He, Y. Tu, S. Wang, F. Zhang, Y. Zhang, H. Li, Angew. Chem. 2012, 124, 8941-8945
29. Angew. Chem. Int. Ed. 2012, 51, 8811-8815.
30. R. D. Richardson, T. Wirth, Angew. Chem. 2006, 118, 4510-4512
31. Angew. Chem. Int. Ed. 2006, 45, 4402-4404
32. M. Ochiai, K. Miyamoto, Eur. J. Org. Chem. 2008, 4229-4235
33. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299-5358
34. V. V. Zhdankin, ARKIVOC 2009, (i), 1-62
35. T. Dohi, Y. Kita, Chem. Commun. 2009, 2073-2085
36. M. Uyanik, K. Ishihara, Chem. Commun. 2009, 2086-2099
37. M. Uyanik, K. Ishihara, ChemCatChem 2012, 4, 177-185
38. M. S. Yusubov, V. V. Zhdankin, Curr. Org. Synth. 2012, 9, 247-272; for recent selected examples on organoiodine-catalyzed oxidative coupling reactions, see
39. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, Y. Kita, Angew. Chem. 2005, 117, 6349-6352
40. Angew. Chem. Int. Ed. 2005, 44, 6193-6196
41. M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, K. Miyamoto, J. Am. Chem. Soc. 2005, 127, 12244-12245
42. M. Uyanik, T. Yasui, K. Ishihara, Bioorg. Med. Chem. Lett. 2009, 19, 3848-3851
43. A. Rodríguez, W. J. Moran, Org. Lett. 2011, 13, 2220-2223
44. M. Ito, H. Kubo, I. Itani, K. Morimoto, T. Dohi, Y. Kita, J. Am. Chem. Soc. 2013, 135, 14078-14081.
45. S. M. Altermann, R. D. Richardson, T. K. Page, R. K. Schmidt, E. Holland, U. Mohammed, S. M. Paradine, A. N. French, C. Richter, A. M. Bahar, B. Witulski, T. Wirth, Eur. J. Org. Chem. 2008, 5315-5328
46. S. Quideau, G. Lyvinec, M. Marguerit, K. Bathany, A. Ozanne-Beaudenon, T. Buffeteau, D. Cavagnat, A. Chenede, Angew. Chem. 2009, 121, 4675-4679
47. Angew. Chem. Int. Ed. 2009, 48, 4605-4609
48. T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita, Angew. Chem. 2008, 120, 3847-3850
49. Angew. Chem. Int. Ed. 2008, 47, 3787-3790
50. M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. 2010, 122, 2221-2223
51. Angew. Chem. Int. Ed. 2010, 49, 2175-2177
52. M. Uyanik, H. Okamoto, T. Yasui, K. Ishihara, Science 2010, 328, 1376-1379
53. K. A. Volp, A. M. Harned, Chem. Commun. 2013, 49, 3001-3003
54. M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. 2013, 125, 9385-9388
55. Angew. Chem. Int. Ed. 2013, 52, 9215-9218.
56. M. Fujita, S. Okuno, H. J. Lee, T. Sugimura, T. Okuyama, Tetrahedron Lett. 2007, 48, 8691-8694
57. M. Fujita, Y. Yoshida, K. Miyata, A. Wakisaka, T. Sugimura, Angew. Chem. 2010, 122, 7222-7225
58. Angew. Chem. Int. Ed. 2010, 49, 7068-7071
59. M. Fujita, M. Wakita, T. Sugimura, Chem. Commun. 2011, 47, 3983-3985
60. C. Röben, J. A. Souto, Y. González, A. Lishchynskyi, K. Muñiz, Angew. Chem. 2011, 123, 9650-9654
61. Angew. Chem. Int. Ed. 2011, 50, 9478-9482
62. U. Farid, T. Wirth, Angew. Chem. 2012, 124, 3518-3522
63. Angew. Chem. Int. Ed. 2012, 51, 3462-3465
64. U. Farid, F. Malmedy, R. Claveau, L. Albers, T. Wirth, Angew. Chem. 2013, 125, 7156-7160
65. Angew. Chem. Int. Ed. 2013, 52, 7018-7022.
66. J. Wang, Y. Yuan, R. Xiong, D. Zhang-Negrerie, Y. Du, K, Zhao, Org. Lett. 2012, 14, 2210-2213.
67. R. M. Moriarty, J. S. Khosrowshahi, O. Prakash, Tetrahedron Lett. 1985, 26, 2961-2964.