Copper-catalyzed aerobic oxidative cleavage of C-C bonds in epoxides leading to aryl ketones

Journal of Organic Chemistry

Volumn 79, Issue 17, 2014, Pages 8453-8456

  Gu, Lijun ^a   Jin, Cheng ^b   Zhang, Hongtao ^a   Zhang, Lizhu ^a  

^a YUNNAN MINZU UNIVERSITY   (China)

^b New United Group Company Limited   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER; SYNTHESIS (CHEMICAL);

ARYL KETONES; C-C BONDS; COPPER CATALYZED; OXIDATIVE CLEAVAGES; SINGLE BOND;

KETONES;

ALKYL ARYL KETONE; COPPER; EPOXIDE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 84919686740     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5013898     Document Type: Article

References (55)

1. Masarwa, A.; Marek, I. Chem.-Eur. J. 2010, 16, 9712
2. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100
3. Seiser, T.; Sage, T.; Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2011, 50, 7740
4. Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300
5. Pohlhaus, P. D.; Bowman, R. K.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 2294
6. Li, G.; Arisawa, M.; Yamaguchi, M. Chem. Commun. 2014, 50, 4328
7. Zhang, C.; Feng, P.; Jiao, N. J. Am. Chem. Soc. 2013, 135, 15257
8. Stevenson, S. M.; Newcomb, E. T.; Ferreira, E. M. Chem. Commun. 2014, 50, 5239
9. Chen, P.; Xu, T.; Dong, G. Angew. Chem., Int. Ed. 2014, 53, 1674
10. Ziaei-Azad, H.; Semagina, N. ChemCatChem 2014, 6, 885
11. Lei, Z.-Q.; Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Sun, J.; Shi, Z.-J. Angew. Chem., Int. Ed. 2012, 51, 2690
12. Youn, S. W.; Kim, B. S.; Jagdale, A. R. J. Am. Chem. Soc. 2012, 134, 11308
13. Chen, W.; Lin, L.; Cai, Y.; Xia, Y.; Cao, W.; Liu, X.; Feng, X. Chem. Commun. 2014, 50, 2161
14. Liu, H.; Dong, C.; Zhang, Z.; Wu, P.; Jiang, X. Angew. Chem., Int. Ed. 2012, 51, 12570
15. Maji, A.; Rana, S.; Akanksha; Maiti, D. Angew. Chem., Int. Ed. 2014, 53, 2428
16. Qin, C.; Shen, T.; Tang, C.; Jiao, N. Angew. Chem., Int. Ed. 2012, 51, 6971
17. Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Shi, Z.-J. J. Am. Chem. Soc. 2011, 133, 15244
18. Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 3518
19. Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862
20. Seisera, T.; Cramer, N. Org. Biomol. Chem. 2009, 7, 2835
21. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051
22. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
23. Rondla, N. R.; Levi, S. M.; Ryss, J. M.; Vanden Berg, R. A.; Douglas, C. J. Org. Lett. 2011, 13, 1940
24. Wang, J.; Chen, W.; Zuo, S.; Liu, L.; Zhang, X.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 12334
25. Boultadakis-Arapinis, M.; Hopkinson, M. N.; Glorius, F. Org. Lett. 2014, 16, 1630
26. Borosky, G. L.; Laali, K. K. Org. Biomol. Chem. 2009, 5, 2234
27. Regati, S.; He, Y.; Thimmaiah, M.; Li, P.; Xiang, S.; Chen, B.; Zhao, J. C. Chem. Commun. 2013, 49, 9836
28. Seth, K.; Roy, S. R.; Pipaliya, B. V.; Chakraborti, A. K. Chem. Commun. 2013, 49, 5886
29. Morimoto, Y.; Takeuchi, E.; Kambara, H.; Kodama, T.; Tachi, Y.; Nishikawa, K. Org. Lett. 2013, 15, 2966
30. Wang, X.; Guo, H.; Liu, M.; Wang, X.; Deng, D. Chin. Chem. Lett. 2014, 25, 243
31. Nie, Y.; You, Q.-D. Chin. Chem. Lett. 2013, 24, 183
32. Chen, Z.; Wei, L.; Zhang, J. Org. Lett. 2011, 13, 1170
33. Wang, T.; Wang, C.; Zhang, J. Chem. Commun. 2011, 47, 5578
34. Chen, Z.; Tian, Z.; Zhang, J.; Ma, J.; Zhang, J. Chem.-Eur. J. 2012, 18, 8591
35. López, M. P.; Neumann, H.; Beller, M. Chem.-Eur. J. 2014, 20, 1818
36. Gu, L.; Jin, C. Org. Biomol. Chem. 2012, 10, 7098
37. Gu, L.; Jin, C.; Guo, J.; Zhang, L.; Wang, W. Chem. Commun. 2013, 49, 10968
38. Gu, L.; Jin, C.; Wang, R.; Ding, H. ChemCatChem 2014, 6, 1225
39. Gu, L.; Liu, J.; Zhang, L.; Xiong, Y.; Wang, R. Chin. Chem. Lett. 2014, 25, 90
40. Gu, L.; Wang, W.; Xiong, Y.; Huang, X.; Li, G. Eur. J. Org. Chem. 2014, 319
41. Dai, M.; Liang, B.; Wang, C.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 221
42. Shi, Z.; Zhang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381
43. Lu, Q.; Zhang, J.; Zhao, G.; Qi, Y.; Wang, H.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481
44. Liang, Y.; Jiao, N. Angew. Chem., Int. Ed. 2014, 53, 548
45. Liu, J.; Liu, Q.; Yi, H.; Qin, Q.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502
46. Cao, Q.; Dornan, L. M.; Rogan, L.; Hughes, N. L.; Muldoon, M. J. Chem. Commun. 2014, 50, 4524
47. Kodama, T.; Harada, S.; Tanaka, T.; Tachi, Y.; Morimoto, Y. Synlett 2012, 23, 458
48. Tiwari, B.; Zhang, J.; Chi, Y. Angew. Chem., Int. Ed. 2012, 51, 1911
49. Bhatt, M. V. Tetrahedron 1964, 20, 803
50. Hine, J.; Haworth, H. W. J. Am. Chem. Soc. 1958, 80, 2274
51. Comisar, C. M.; Savage, P. E. Green Chem. 2005, 7, 800
52. Li, M.; Wang, C.; Ge, H. Org. Lett. 2011, 13, 2062
53. Cai, M.; Zheng, G.; Zhang, L.; Peng, J. Eur. J. Org. Chem. 2009, 1585
54. Boroujeni, K. P. Chin. Chem. Lett. 2010, 21, 1395
55. Xin, B.; Zhang, Y.; Cheng, K. J. Org. Chem. 2006, 71, 5725