Copper-catalyzed Csp3-O cross-coupling of unactivated alkyl halides with organic peroxides

Tetrahedron

Volumn 70, Issue 2, 2014, Pages 212-217

  Chen, Huan Huan ^a,b   Wang, Guang Zu ^a,b   Han, Jin ^a,b   Xu, Meng Yu ^a,b   Zhao, Yong Qiang ^a,b   Xu, Hua Jian ^a,b  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

^b KEY LABORATORY OF ADVANCED FUNCTIONAL MATERIALS AND DEVICES OF ANHUI PROVINCE   (China)

Author keywords

Aryl alkyl esters; Csp3 O coupling; Copper catalyzed; Organic peroxides; Secondary alkyl halides

Indexed keywords

ALKANE DERIVATIVE; ALKYL GROUP; COPPER; HALIDE; ORGANOHALOGEN DERIVATIVE; PEROXIDE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; ORGANIC CHEMISTRY; PRIORITY JOURNAL;

EID: 84890807551     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.11.085     Document Type: Article

References (57)

1. M. Beller, and A. Zapf Top. Catal. 19 2002 101
2. J. Stetter, and F. Lieb Angew. Chem., Int. Ed. 39 2000 1724
3. T. Efferth, H. Dunstan, A. Sauerbrey, H. Miyachi, and C.R. Chitambar Int. J. Oncol. 18 2001 767
4. Y. Li, F. Shan, J.-M. Wu, G.-S. Wu, J. Ding, D. Xiao, W.-Y. Yang, G. Atassi, S. Leonce, D.-H. Caignard, and P. Renard Bioorg. Med. Chem. Lett. 11 2001 5
5. A.C. Beekman, H.J. Woerdenbag, U.W. Van, N. Pras, A.W.T. Konings, and H.V. Wikstrom J. Pharm. Pharmacol. 49 1997 1254
6. S. Sakemi, T. Higa, U. Anthony, and C. Christophersen Tetrahedron 43 1987 263
7. f. Huang, T.D. Quach, and R.A. Batey Org. Lett. 15 2013 3150
8. F. Luo, C.D. Pan, and J. Cheng Synlett 2012 357
9. C. Liu, S. Tang, L.-W. Zheng, D. Liu, H. Zhang, and A.-W. Lei Angew. Chem., Int. Ed. 51 2012 5662
10. Y.-Q. Cao, G.-Q. Wu, Y.-B. Li, Z. Li, and B.-H. Chen Synth. Commun. 36 2006 3353
11. P.B. Sean, L.H. David, and V. Sunil J. Org. Chem. 71 2006 7881
12. T.G. Raymond, L.M. Claire, G.S. Nicholas, S.J. Eun, J.B.A. Mae, R.C. Thomas, and H.W. Timothy J. Am. Chem. Soc. 134 2012 17350
13. K. Dany, C. Alain, L. Jean-Pierre, and G.-A. Elena J. Org. Chem. 76 2011 6188
14. M.S. Daniel, A.B. Marc, and C.V. John Org. Lett. 11 2009 645
15. I.N. Grebenshchikov, A.S. Dykman, and V.V. Pinson Russ. J. Org. Chem. 44 2008 617
16. X.-F. Ren, J.-L. Xu, and S.-H. Chen Chin. J. Org. Chem. 26 2006 454
17. U. Polona, W.S. Jin, H. Klara, M. Ales, P. Peter, D.M. Dragan, and F. Lá szló Chem. Mater. 15 2003 4751
18. G.A. Razuvaev Zh. Obshch. Khim. 31 1961 2340
19. A. Capretta, V. Laritchev, J. Dyck, and A.J. Robertson Angew. Chem., Int. Ed. 42 2003 4051
20. M. Anne, and A.E. Slayton Jr. J. Org. Chem. 53 1988 2300
21. K. Taichi, M. Haruka, and M. Keiji J. Am. Chem. Soc. 131 2009 3450
22. J.P.V. Matti, C.Y. Sze, and C.O.T. Nicholas Tetrahedron Lett. 50 2009 3625
23. G. Hiroaki, and H. Yujiro Chem. Commun. 2009 3083
24. H. Philippe, P. Francois, T. Christine, and G. Christine Tetrahedron Lett. 54 2013 1052
25. D. Nicolas, L. Olga, and L. Benjamin Tetrahedron 68 2012 7568
26. Y.-J. Jiang, J. Wu, Y.-F. Lin, and C.-F. Yao Tetrahedron 60 2004 6565
27. L. Olga, D. Nicolas, and L. Benjamin Angew. Chem., Int. Ed. 50 2011 9680
28. S.J. Milind, R. Paolo, M. Enrico, and B. Giorgio J. Org. Chem. 77 2012 2667
29. J.-J. Dai, C. Fang, B. Xiao, J. Yi, J. Xu, Z.-J. Liu, X. Lu, L. Liu, and Y. Fu J. Am. Chem. Soc. 135 2013 8436
30. Z. Li, D.S. Bohle, and C.J. Li Proc. Natl. Acad. Sci. U.S.A. 103 2006 8928
31. X. Chen, X.S. Hao, C.E. Goodhue, and J.Q. Yu J. Am. Chem. Soc. 128 2006 6790
32. T. Uemura, S. Imoto, and N. Chatani Chem. Lett. 35 2006 842
33. Z. Li, and C.-J. Li J. Am. Chem. Soc. 127 2005 6968
34. W. Zeng, and S.R. Chemler J. Am. Chem. Soc. 129 2007 12948
35. E.S. Sherman, P.H. Fuller, D. Kasi, and S.R. Chemler J. Org. Chem. 72 2007 3896
36. P.H. Fuller, and S.R. Chemler Org. Lett. 9 2007 5477
37. C.-T. Yang, Z.-Q. Zhang, J. Liang, J.-H. Liu, X.-Y. Lu, H.-H. Chen, and L. Liu J. Am. Chem. Soc. 134 2012 11124
38. Y. Kohmura, and T. Katsuki Tetrahedron Lett. 41 2000 3941
39. Y. Kohmura, and T. Katsuki Synlett 1999 1231
40. Q. Shuai, G. Deng, Z. Chua, D.S. Bohle, and C.-J. Li Adv. Synth. Catal. 352 2010 632
41. E.J. Park, S.H. Kim, and S. Chang J. Am. Chem. Soc. 130 2008 17268
42. T. Xiong, Y. Li, X. Bi, Y. Lv, and Q. Zhang Angew. Chem., Int. Ed. 50 2011 7140
43. C.-T. Yang, Z.-Q. Zhang, Y.-C. Liu, and L. Liu Angew. Chem., Int. Ed. 50 2011 3904
44. F. Bellina, and S. Rossi Adv. Synth. Catal. 352 2010 1223
45. M.J. Moure, R. SanMartin, and E. Dominguez Angew. Chem., Int. Ed. 124 2012 3274
46. E. Stephan, and W. Maik ChemSusChem 5 2012 1195
47. B.C. John, and A.K. Frederick J. Am. Chem. Soc. 60 1938 129
48. U. Rui, N. Takashi, and N. Yutaka Tetrahedron 67 2011 7217
49. A.M. Gary, and N.C. Livia J. Org. Chem. 76 2011 7195
50. M.W. Henry, and E.S. Cyrus J. Am. Chem. Soc. 71 1949 1709
51. P.K. Lester, and H.C. Alsoph J. Am. Chem. Soc. 70 1948 3370
52. S.P. Aviraboina, and S. Bollikonda J. Mol. Catal. A: Chem. 370 2013 205
53. S.P. Hangirgekar Int. J. ChemTech Res. 4 2012 651
54. M. Kuchar, H. Tomkova, V. Rejholec, and O.O. Ilpo J. Chromatogr. 356 1986 95
55. O. Fumiyuki, and K. Nobuo Chem. Lett. 14 1985 567
56. Levorse, A. T., Jr.; Weiss, R. A. Methylcyclohexanecarboxylates and their use in perfume compositions: U.S. Patent 20,090,131,301, 2009-05-21.
57. E.H. White J. Am. Chem. Soc. 77 1955 6014