Metal-free oxidative direct C(sp3)–H bond functionalization of ethers with α,α-diaryl allylic alcohols

Chemical Communications

Volumn 50, Issue 68, 2014, Pages 9718-9721

  Chu, Xue Qiang ^a   Meng, Hua ^a   Zi, You ^a   Xu, Xiao Ping ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALPHA ARYL BETA OXYALKYLATED CARBONYL KETONE DERIVATIVE; ALPHA,ALPHA DIARYL ALLYLIC ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; METAL FREE OXIDATIVE DIRECT C H BOND FUNCTIONALIZATION; RADICAL REACTION;

EID: 84904976835     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc04282d     Document Type: Article

References (69)

1. Handbook of C–H Transformations, ed. G. Dyker, Wiley-VCH, Weinheim, 2005
2. Topics in Current Chemistry: C-H Activation, ed. J.-Q. Yu and Z.-J. Shi, Springer, 2010, vol. 292
3. A. K. Yudin and J. F. Hartwig, Catalyzed Carbon-Heteroatom Bond Formation, Wiley-VCH, Weinheim, 2010
4. O. Daugulis, H. Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
5. I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890
6. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
7. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293
8. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
9. H. M. Davies, J. D. Bois, J.-Q. Yu, Chem. Soc. Rev. 2011, 40, 1855
10. S. I. Kozhushkov, L. Ackermann, Chem. Sci. 2013, 4, 886
11. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780
12. K. R. Campos, Chem. Soc. Rev. 2007, 36, 1069
13. S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. Int. Ed. 2014, 53, 74
14. S. Chiba, H. Chen, Org. Biomol. Chem. 2014, 12, 4051
15. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 56
16. C. He, S. Guo, J. Ke, J. Hao, H. Xu, H. Chen, A. Lei, J. Am. Chem. Soc. 2012, 134, 5766
17. K. Alagiri, P. Devadig, K. R. Prabhu, Chem. – Eur. J. 2012, 18, 5160
18. Z. Cui, X. Shang, X.-F. Shao, Z.-Q. Liu, Chem. Sci. 2012, 3, 2853
19. J. Zhang, B. Tiwari, C. Xing, X. Chen, Y. R. Chi, Angew. Chem. Int. Ed. 2012, 51, 3649
20. T. Sugiishi, H. Nakamura, J. Am. Chem. Soc. 2012, 134, 2504
21. E. Shi, Y. Shao, S. Chen, H. Hu, Z. Liu, J. Zhang, X. Wan, Org. Lett. 2012, 14, 3384
22. A. P. Antonchick, L. Burgmann, Angew. Chem. Int. Ed. 2013, 52, 3267
23. M.-B. Zhou, C.-Y. Wang, R.-J. Song, Y. Liu, W.-Y. Wei, J.-H. Li, Chem. Commun. 2013, 49, 10817
24. H. Liu, G. Shi, S. Pan, Y. Jiang, Y. Zhang, Org. Lett. 2013, 15, 4098
25. P. Xie, C. Xia, H. Huang, Org. Lett. 2013, 15, 3370
26. S.-Y. Zhang, G. He, W. A. Nack, Y. Zhao, Q. Li, G. Chen, J. Am. Chem. Soc. 2013, 135, 2124
27. S.-L. Zhou, L.-N. Guo, S. Wang, X.-H. Duan, Chem. Commun. 2014, 50, 3589
28. Z. Li, Y. Zhang, L. Zhang, Z.-Q. Liu, Org. Lett. 2014, 16, 382
29. C.-J. Li, Acc. Chem. Res. 2008, 42, 335
30. S.-Y. Zhang, F.-M. Zhang, Y.-Q. Tu, Chem. Soc. Rev. 2011, 40, 1937
31. Y.-J. Jang, Y.-K. Shih, J.-Y. Liu, W.-Y. Kuo, C.-F. Yao, Chem. – Eur. J. 2003, 9, 2123
32. X.-F. Huang, T. He, L. Yu, L. Zhang, L. Wang, M. Wang, Org. Lett. 2011, 13, 5016
33. S. Zhang, L.-N. Guo, H. Wang, X.-H. Duan, Org. Biomol. Chem. 2013, 11, 4308
34. X.-F. Huang, Z.-Q. Zhu, Z.-Z. Huang, Tetrahedron, 2013, 69, 8579
35. D. Liu, C. Liu, H. Li, A. Lei, Angew. Chem. Int. Ed. 2013, 52, 4453
36. Z. Xie, Y. Cai, H. Hu, C. Lin, J. Jiang, Z. Chen, L. Wang, Y. Pan, Org. Lett. 2013, 15, 4600
37. J. Zhang, P. Li, L. Wang, Org. Biomol. Chem. 2014, 12, 2969
38. L. Troisi, C. Granito, L. Ronzini, F. Rosato, V. Videtta, Tetrahedron Lett. 2010, 51, 5980
39. L. Chen, E. Shi, Z. Liu, S. Chen, W. Wei, H. Li, K. Xu, X. Wan, Chem. – Eur. J. 2011, 17, 4085
40. G. S. Kumar, B. Pieber, K. R. Reddy, C. O. Kappe, Chem. – Eur. J. 2012, 18, 6124
41. B. D. Barve, Y.-C. Wu, M. El-Shazly, M. Korinek, Y.-B. Cheng, J.-J. Wang, F.-R. Chang, Org. Lett. 2014, 16, 1912
42. S. Pan, J. Liu, H. Li, Z. Wang, X. Guo, Z. Li, Org. Lett. 2010, 12, 1932
43. S.-R. Guo, Y.-Q. Yuan, J.-N. Xiang, Org. Lett. 2013, 15, 4654
44. K. Cheng, L. Huang, Y. Zhang, Org. Lett. 2009, 11, 2908
45. H. Sun, Y. Zhang, F. Guo, Z. Zha, Z. Wang, J. Org. Chem. 2012, 77, 3563
46. W.-T. Wei, M.-B. Zhou, J.-H. Fan, W. Liu, R.-J. Song, Y. Liu, M. Hu, P. Xie, J.-H. Li, Angew. Chem. Int. Ed. 2013, 52, 3638
47. D. Liu, C. Liu, H. Li, A. Lei, Chem. Commun. 2014, 50, 3623
48. J.-J. Cao, T.-H. Zhu, S.-Y. Wang, Z.-Y. Gu, X. Wang, S.-J. Ji, Chem. Commun. 2014, 50, 6439
49. L. Wang, W. Sha, Q. Dai, X. Feng, W. Wu, H. Peng, B. Chen, J. Cheng, Org. Lett. 2014, 16, 2088
50. C. J. Dutton, B. J. Banks, C. B. Cooper, Nat. Prod. Rep. 1995, 12, 165
51. K. S. Yeung, I. Paterson, Chem. Rev. 2005, 105, 4237
52. T. Nakata, Chem. Rev. 2005, 105, 4314
53. A. Bermejo, B. Figadere, M. C. Zafra-Polo, I. Barrachina, E. Estornell, D. Cortes, Nat. Prod. Rep. 2005, 22, 269
54. V. Mammoli, A. Bonifazi, F. Del Bello, E. Diamanti, M. Giannella, A. L. Hudson, L. Mattioli, M. Perfumi, A. Piergentili, W. Quaglia, F. Titomanlio, M. Pigini, Bioorg. Med. Chem. 2012, 20, 2259
55. T. D. Kohlman, Y.-C. Xu, A. G. Godfrey, J. C. O'Toole, T. Y. Zhang, Eur. Pat. Appl. 1999, 47
56. C. Rüchardt, R. Hecht, Chem. Ber. 1965, 98, 2471
57. M. Tada, K. Inoue, M. Okabe, Bull. Chem. Soc. Jpn. 1983, 56, 1420
58. C. S. A. Antunes, M. Bietti, G. Ercolani, O. Lanzalunga, M. Salamone, J. Org. Chem. 2005, 70, 3884
59. X. Liu, F. Xiong, X. Huang, L. Xu, P. Li, X. Wu, Angew. Chem. Int. Ed. 2013, 52, 6962
60. H. Egami, R. Shimizu, Y. Usui, M. Sodeoka, Chem. Commun. 2013, 49, 7346
61. Z.-M. Chen, W. Bai, S.-H. Wang, B.-M. Yang, Y.-Q. Tu, F.-M. Zhang, Angew. Chem. Int. Ed. 2013, 52, 9781
62. T.-H. Zhu, X.-P. Xu, J.-J. Cao, T.-Q. Wei, S.-Y. Wang, S.-J. Ji, Adv. Synth. Catal. 2014, 356, 509
63. T.-H. Zhu, S.-Y. Wang, Y.-Q. Tao, T.-Q. Wei, S.-J. Ji, Org. Lett. 2014, 16, 1260
64. T.-H. Zhu, S.-Y. Wang, G.-N. Wang, S.-J. Ji, Chem. – Eur. J. 2013, 19, 5850
65. Y. Zi, Z.-J. Cai, S.-Y. Wang, S.-J. Ji, Org. Lett. 2014, 16, 3094
66. X.-Q. Chu, Y. Zi, H. Meng, X.-P. Xu, S.-J. Ji, Chem. Commun. 2014, 50, 7642
67. K. Rasmussen, D. O. Calligaro, J. F. Czachura, L. J. Dreshfield-Ahmad, D. C. Evans, S. K. Hemrick-Luecke, M. J. Kallman, W. T. Kendrick, J. D. Leander, D. L. Nelson, C. D. Overshiner, D. B. Wainscott, M. C. Wolff, D. T. Wong, T. A. Branchek, J. M. Zgombick, Y.-C. Xu, J. Pharmacol. Exp. Ther. 2000, 294, 688
68. S. E. Denmark, J. Fu, Org. Lett. 2002, 4, 1951
69. S. Muthusamy, P. Srinivasan, Tetrahedron Lett. 2006, 47, 6297