Copper-catalyzed oxidative coupling of acids with alkanes involving dehydrogenation: Facile access to allylic esters and alkylalkenes

Chemical Communications

Volumn 51, Issue 12, 2015, Pages 2361-2363

  Wang, Cheng Yong ^a   Song, Ren Jie ^a   Wei, Wen Ting ^a   Fan, Jian Hong ^a   Li, Jin Heng ^a  

^a HUNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKENE; ALKYLALKENE; COPPER; ESTER; UNCLASSIFIED DRUG; CARBON;

ARTICLE; CONTROLLED STUDY; COVALENT BOND; DEHYDROGENATION; ESTERIFICATION; OXIDATION; OXIDATIVE COUPLING; SYNTHESIS; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKANES; CARBON; CATALYSIS; COPPER; ESTERIFICATION; ESTERS; OXIDATIVE COUPLING; STEREOISOMERISM;

EID: 84921869950     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc09393c     Document Type: Article

References (68)

1. (a) P. Adams and F. A. Baron, Chem. Rev., 1965, 65, 567;
2. (b) W. Riemenschneider and H. M. Bolt, Esters, Organic. Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005;
3. (c) J. Mulzer, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, New York, 1992, vol. 6;
4. (d) R. C. Larock, Comprehensive Organic Transformations, Wiley-VCH, New York, 2nd edn, 1999;
5. (e) J. Otera, Esterification: Methods, Reactions, and Applications, Wiley-VCH, Weinheim, 2003;
6. (f) K. C. K. Swamy, N. N. B. Kumar, E. Balaraman and K. V. P. P. Kumar, Chem. Rev., 2009, 109, 2551.
7. (a) L. S. Kheang and C. Y. May, J. Oil Palm Res., 2012, 24, 1388;
8. (b) A. Mittal and M. Ali, Pharm. Lett., 2012, 4, 1461;
9. (c) E. Makrlík, P. Selucký and P. Vaňura, J. Mol. Liq., 2013, 180, 221;
10. (d) K. Malins, V. Kampars, J. Brinks, T. Rusakova and Z. Sustere, Materialzinat. Lietiska Kim., 2012, 25, 9;
11. (e) A. X. Zeng, S.-T. Chin and P. J. Marriott, J. Sep. Sci., 2013, 36, 878;
12. (f) L. Zheng, D. Li, X. Xiang, L. Tong, M. Qi, J. Pu, K. Huang and Q. Tong, BMC Cancer, 2013, 13, 74.
13. (a) L. V. Desai, K. L. Hull and M. S. Sanford, J. Am. Chem. Soc., 2004, 126, 9542;
14. (b) S. R. Neufeldt and M. S. Sanford, Org. Lett., 2010, 12, 532;
15. (c) R. Giri, J. Liang, J.-G. Lei, J.-J. Li, D.-H. Wang, X. Chen, I. C. Naggar, C. Guo, B. M. Foxman and J.-Q. Yu, Angew. Chem., Int. Ed., 2005, 44, 7420;
16. (d) B. V. S. Reddy, L. R. Reddy and E. J. Corey, Org. Lett., 2006, 8, 3391;
17. (e) K. J. Stowers, A. Kubota and M. S. Sanford, Chem. Sci., 2012, 3, 3192;
18. (f) E. M. Simmons and J. F. Hartwig, Nature, 2012, 483, 70;
19. (g) S.-Y. Zhang, G. He, Y. Zhao, K. Wright, W. A. Nack and G. Chen, J. Am. Chem. Soc., 2012, 134, 7313;
20. (h) R. K. Rit, R. Yadav and A. K. Sahoo, Org. Lett., 2012, 14, 3724;
21. (i) Z. Ren, F. Mo and G. Dong, J. Am. Chem. Soc., 2012, 134, 16991;
22. (j) F.-J. Chen, S. Zhao, F. Hu, K. Chen, Q. Zhang, S.-Q. Zhang and B.-F. Shi, Chem. Sci., 2013, 4, 4187;
23. (k) L. Zhou and W. Lu, Org. Lett., 2014, 16, 508.
24. (a) G. Majji, S. Guin, A. Gogoi, S. K. Rout and B. K. Patel, Chem. Commun., 2013, 49, 3031;
25. (b) Y.-J. Bian, C.-B. Xiang, Z.-M. Chen and Z.-Z. Huang, Synlett, 2011, 2407;
26. (c) S. K. Rout, S. Guin, A. Banerjee, N. Khatun, A. Gogoi and B. K. Patel, Org. Lett., 2013, 15, 4106;
27. (d) S. K. Rout, S. Guin, K. K. Ghara, A. Banerjee and B. K. Patel, Org. Lett., 2012, 14, 3982;
28. (e) S. Guin, S. K. Rout, A. Banerjee, S. Nandi and B. K. Patel, Org. Lett., 2012, 14, 5294;
29. (f) Z. Yin and P. Sun, J. Org. Chem., 2012, 77, 11339;
30. (g) Y. Wu, P. Y. Choy, F. Mao and F. Y. Kwong, Chem. Commun., 2013, 49, 689;
31. (h) D. L. Priebbenow and C. Bolm, Org. Lett., 2014, 16, 1650;
32. (i) R. Vanjari, T. Guntreddi and K. N. Singh, Org. Lett., 2013, 15, 4908;
33. (j) H. Liu, G. Shi, S. Pan, Y. Jiang and Y. Zhang, Org. Lett., 2013, 15, 4098;
34. (k) L. Ju, J. Yao, Z. Wu, Z. Liu and Y. Zhang, J. Org. Chem., 2013, 78, 10821;
35. (l) L. Liu, L. Yun, Z. Wang, X. Fu and C.-h. Yan, Tetrahedron Lett., 2013, 54, 5383;
36. (m) S. K. Rout, S. Guin, W. Ali, A. Gogoi and B. K. Patel, Org. Lett., 2014, 16, 3086;
37. (n) J. Zhao, H. Fang, J. Han and Y. Pan, Org. Lett., 2014, 16, 2530;
38. (o) B. L. Tran, M. Driess and J. F. Hartwig, J. Am. Chem. Soc., 2014, 136, 17292.
39. (a) J. Zhao, H. Fang, W. Zhou, J. Han and Y. Pan, J. Org. Chem., 2014, 79, 3847;
40. (b) M. S. Kharasch and G. Sosnovsky, J. Am. Chem. Soc., 1958, 80, 756;
41. (c) M. S. Kharasch, G. Sosnovsky and N. C. Yang, J. Am. Chem. Soc., 1959, 81, 5819;
42. (d) J. Eames and M. Watkinson, Angew. Chem., Int. Ed., 2001, 40, 3567.
43. (a) C.-J. Li, Acc. Chem. Res., 2009, 42, 335;
44. (b) G. P. Mcglacken, L. M. Bateman and L. Bateman, Chem. Soc. Rev., 2009, 38, 2447;
45. (c) D. Shabashov, Acc. Chem. Res., 2009, 42, 1074;
46. (d) J. A. Ashenhurst, Chem. Soc. Rev., 2010, 39, 540;
47. (e) S. H. Cho, J. Y. Kim, J. Kwak and S. Chang, Chem. Soc. Rev., 2011, 40, 5068;
48. (f) J. Le Bras and J. Muzart, Chem. Rev., 2011, 111, 1170;
49. (g) C. Liu, H. Zhang, W. Shi and A. Lei, Chem. Rev., 2011, 111, 1780;
50. (h) Y.-X. Xie, R.-J. Song, J.-N. Xiang and J.-H. Li, Chin. J. Org. Chem., 2012, 32, 1555;
51. (i) C. Zhang, C. Tang and N. Jiao, Chem. Soc. Rev., 2012, 41, 3464;
52. (j) F. Guo, M. D. Clift and R. J. Thomson, Eur. J. Org. Chem., 2012, 4881;
53. (k) M. Grzybowski, K. Skonieczny, H. Butenschön and D. T. Gryko, Angew. Chem., Int. Ed., 2013, 52, 9900;
54. (l) S. A. Girard, T. Knauber and C.-J. Li, Angew. Chem., Int. Ed., 2014, 53, 74;
55. (m) S. V. Ley and A. W. Thomas, Angew. Chem., Int. Ed., 2003, 42, 5400.
56. (a) M. Kharasch and G. Sosnovsky, J. Am. Chem. Soc., 1958, 80, 756;
57. (b) M. Kharasch, G. Sosnovsky and N. Yang, J. Am. Chem. Soc., 1959, 81, 5819;
58. (c) J. K. Kochi and H. E. Mains, J. Org. Chem., 1965, 30, 1862;
59. (d) J. Eames and M. Watkinson, Angew. Chem., Int. Ed., 2001, 40, 3567;
60. (e) Q. Tan and M. Hayashi, Adv. Synth. Catal., 2008, 350, 2639;
61. (f) Z. Zhou and M. B. Andrus, Tetrahedron Lett., 2012, 53, 4518;
62. (g) B. Zhang, S. F. Zhu and Q. L. Zhou, Tetrahedron Lett., 2013, 54, 2665.
63. A. Conde, L. Vilella, D. Balcells, M. M. Díaz-Requejo, A. Lledós and P. J. Pérez, J. Am. Chem. Soc., 2013, 135, 3887.
64. (a) J. Zhao, W. Zhou, J. Han, G. Li and Y. Pan, Tetrahedron Lett., 2013, 54, 6507;
65. (b) Z. Cui, X. Shang, X.-F. Shao and Z.-Q. Liu, Chem. Sci., 2012, 3, 2853.
66. (a) A. Studer, Chem. - Eur. J., 2001, 7, 1159;
67. (b) A. Studer, Chem. Soc. Rev., 2004, 33, 267;
68. (c) X.-H. Yang, W.-T. Wei, H.-B. Li, R.-J. Song and J.-H. Li, Chem. Commun., 2014, 50, 12867.