Copper-catalyzed coupling of oxime acetates with sodium sulfinates: An efficient synthesis of sulfone derivatives

Angewandte Chemie - International Edition

Volumn 53, Issue 16, 2014, Pages 4205-4208

  Tang, Xiaodong ^a   Huang, Liangbin ^a   Xu, Yanli ^a   Yang, Jidan ^a   Wu, Wanqing ^a   Jiang, Huanfeng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

C H activation; cleavage reactions; copper; sulfone derivatives

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CHEMICAL BONDS; COPPER; HYDROLYSIS; OXIDANTS; SILICA GEL; SODIUM;

C-H ACTIVATION; C-S BOND FORMATIONS; CLEAVAGE REACTION; COPPER-CATALYZED COUPLINGS; EFFICIENT SYNTHESIS; OPTIMIZED REACTION CONDITIONS; OXIDATIVE COUPLINGS; SYNTHETIC INTERMEDIATES;

COPPER COMPOUNDS;

EID: 84898639262     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201311217     Document Type: Article

References (64)

1. C. J. Li, B. M. Trost, Proc. Natl. Acad. Sci. USA 2008, 105, 13197
2. P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
3. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780
4. C. Li, Acc. Chem. Res. 2009, 42, 155
5. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
6. W. Q. Wu, H. F. Jiang, Acc. Chem. Res. 2012, 45, 1736
7. J. Zhou, G. Wu, M. Zhang, X. Jie, W. P. Su, Chem. Eur. J. 2012, 18, 8032
8. Y. Shang, X. Jie, J. Zhou, P. Hu, S. Huang, W. P. Su, Angew. Chem. 2013, 125, 1337
9. Angew. Chem. Int. Ed. 2013, 52, 1299.
10. F. Cavani, J. H. Teles, ChemSusChem 2009, 2, 508
11. S. Caron, R. W. Dugger, S. G. Ruggeri, J. A. Ragan, D. H. B. Ripin, Chem. Rev. 2006, 106, 2943.
12. A. E. Wendlandt, A. M. Suess, S. S. Stahl, Angew. Chem. 2011, 123, 11256
13. Angew. Chem. Int. Ed. 2011, 50, 11062
14. C. Zhang, C. Tanga, N. Jiao, Chem. Soc. Rev. 2012, 41, 3464
15. P. Gamez, P. G. Aubel, W. L. Driessen, J. Reedijk, Chem. Soc. Rev. 2001, 30, 376
16. Y. Zhang, Z. Chen, W. Wu, Y. Zhang W. P. Su, J. Org. Chem. 2013, 78, 12494.
17. C. L. Sun, B. J. Li, Z. J. Shi, Chem. Rev. 2011, 111, 1293
18. C. Bolm, J. Legros, J. L. Paih, L. Zani, Chem. Rev. 2004, 104, 6217
19. A. Correa, O. G. Mancheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108.
20. Z. Z. Shi, C. Zhang, C. H. Tanga, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381
21. L. Boisvert, K. I. Goldberg, Acc. Chem. Res. 2012, 45, 899
22. A. N. Campbell, S. S. Stall, Acc. Chem. Res. 2012, 45, 851.
23. J. Wu, X. Cui, L. Chen, G. Jiang, Y. Wu, J. Am. Chem. Soc. 2009, 131, 13888
24. B. Liu, C. Song, C. Sun, S. Zhou, J. Zhu, J. Am. Chem. Soc. 2013, 135, 16625.
25. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350
26. N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449
27. L. Xu, Q. Zhu, G. P. Huang, B. Cheng, Y. Z. Xia, J. Org. Chem. 2012, 77, 3017.
28. T. Gerfaud, L. Neuville, J. Zhu, Angew. Chem. 2009, 121, 580
29. Angew. Chem. Int. Ed. 2009, 48, 572
30. Y. Tan, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 3676
31. P. C. Too, S. H. Chua, S. H. Wong, S. Chiba, J. Org. Chem. 2011, 76, 6159
32. P. C. Too, Y. Wang, S. Chiba, Org. Lett. 2010, 12, 5688
33. J. M. Neely, T. Rovis, J. Am. Chem. Soc. 2013, 135, 66
34. W. Tang, A. Capacci, M. Sarvestani, X. Wei, N. K. Yee, C. H. Senanayake, J. Org. Chem. 2009, 74, 9528
35. M. J. Burk, G. Casy, N. B. Johnson, J. Org. Chem. 1998, 63, 6084
36. P. De, Nonappa, K. Pandurangan, U. Maitra, S. Wailes, Org. Lett. 2007, 9, 2767
37. A. John, K. M. Nicholas, Organometallics 2012, 31, 7914
38. S. Liu, Y. Yu, L. S. Liebeskind, Org. Lett. 2007, 9, 1947.
39. H. Yang, R. G. Carter, L. N. Zakharov, J. Am. Chem. Soc. 2008, 130, 9238.
40. J. L. Marco, J. Org. Chem. 1997, 62, 6575
41. J. L. Marco, I. Fernández, N. Khiar, P. Fernández, A. Romero, J. Org. Chem. 1995, 60, 6678.
42. R. E. Swenson, T. J. Sowin, H. Q. Zhang, J. Org. Chem. 2002, 67, 9182.
43. P. A. Bartlett, F. R. Green, E. H. Rose, J. Am. Chem. Soc. 1978, 100, 4852.
44. A. R. Katritzky, A. A. A. Abdel-Fattah, M. Wang, J. Org. Chem. 2003, 68, 1443
45. N. Suryakiran, P. Prabhakar, K. Rajesh, V. Suresh, Y. Venkateswarlu, J. Mol. Catal. A 2007, 207, 201
46. C. Curti, M. Laget, A. O. Carle, A. Gellis, P. Vanelle, Eur. J. Med. Chem. 2007, 42, 880
47. H. Loghmani-Khouzani, M. R. Poorheravi, M. M. M. Sadeghi, L. Caggiano, R. F. W. Jackson, Tetrahedron 2008, 64, 7419
48. D. Kumar, S. Sundaree, V. S. Raoa, R. S. Varma, Tetrahedron Lett. 2006, 47, 4197
49. N. Suryakiran, T. Srikanth Reddy, K. Ashalatha, M. Lakshman, Y. Venkateswarlu, Tetrahedron Lett. 2006, 47, 3853
50. A. Kumar, M. K. Muthyala, Tetrahedron Lett. 2011, 52, 5368
51. Q. Lu, J. Zhang, G. Zhao, Y. Qi, H. Wang, A. Lei, J. Am. Chem. Soc. 2013, 135, 11481
52. M. W. Thomsen, B. M. Handwerker, S. A. Katz, R. B. Belser, J. Org. Chem. 1988, 53, 906.
53. X. D. Tang, L. B. Huang, C. R. Qi, X. Wu, W. Q. Wu, H. F. Jiang, Chem. Commun. 2013, 49, 6102
54. X. D. Tang, L. B. Huang, C. R. Qi, W. Q. Wu, H. F. Jiang, Chem. Commun. 2013, 49, 9597
55. L. B. Huang, H. F. Jiang, C. R. Qi, X. H. Liu, J. Am. Chem. Soc. 2010, 132, 17652
56. X. W. Li, L. B. Huang, H. J. Chen, W. Q. Wu, H. W. Huang, H. F. Jiang, Chem. Sci. 2012, 3, 3463
57. H. F. Jiang, W. Zeng, Y. B. Li, W. Q. Wu, L. B. Huang, W. Fu, J. Org. Chem. 2012, 77, 5179
58. H. W. Huang, X. C. Ji, W. Q. Wu, L. B. Huang, H. F. Jiang, J. Org. Chem. 2013, 78, 3374.
59. CCDC 965756 (3 ta) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. A single crystal of product 3 ta is in Supporting Information.
60. G. C. Tsui, Q. Glenadel, C. Lau, M. Lautens, Org. Lett. 2011, 13, 208.
61. B. L. Feringa, J. Chem. Soc. Chem. Commun. 1985, 466.
62. Y. Wei, N. Yoshikai, J. Am. Chem. Soc. 2013, 135, 3756
63. Z. H. Ren, Z. Y. Zhang, B. Q. Yang, Y. Y. Wang, Z. H. Guan, Org. Lett. 2011, 13, 5394.
64. H. Liang, Z. Ren, Y. Y. Wang, Z. Guan, Chem. Eur. J. 2013, 19, 9789.