A direct approach to β-keto sulfones via AgNO3/K2S2O8catalyzed aerobic oxysulfonylation of alkenes in aqueous medium

Tetrahedron Letters

Volumn 55, Issue 34, 2014, Pages 4742-4746

  Singh, Atul K ^a   Chawla, Ruchi ^a   Yadav, Lal Dhar S ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

Author keywords

Aerobic oxysulfonylation; AgNO3 K2S2O8catalysis; Alkenes; Sodium arenesulfinates; Keto sulfones

Indexed keywords

ALKENE; ARENESULFINATE SALT; BETA KETO SULFONE; INORGANIC SALT; OXYGEN; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

AEROBIC OXYSULFONYLATION; AIR; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; ENVIRONMENTAL TEMPERATURE; MATERIALS; ONE POT SYNTHESIS; RADICAL REACTION;

EID: 84906082107     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.06.086     Document Type: Article

References (55)

1. T. Punniyamurthy, S. Velusamy, and J. Iqbal Chem. Rev. 105 2005 2329
2. A.E. Wendlandt, A.M. Suess, and S.S. Stahl Angew. Chem., Int. Ed. 50 2011 11062
3. Z. Shi, C. Zhang, C. Tang, and N. Jiao Chem. Soc. Rev. 41 2012 3381
4. W. Wu, H. Jiang, and S. Adimurthy Acc. Chem. Res. 45 2012 1736
5. E.I. Solomon, P. Chen, M. Metz, S.-K. Lee, and A.E. Palmer Angew. Chem., Int. Ed. 40 2001 4570
6. E.I. Solomon, U.M. Sundaram, and T.E. Machonkin Chem. Rev. 96 1996 2563
7. J. Piera, and J.-E. Backvall Angew. Chem., Int. Ed. 47 2008 3506
8. For selected examples, see: Y.-H. Zhang, and J.-Q. Yu J. Am. Chem. Soc. 131 2009 14654
9. A. Wang, and H. Jiang J. Am. Chem. Soc. 130 2008 5030
10. E.A. Lewis, and W.B. Tolman Chem. Rev. 104 2004 1047
11. L.M. Mirica, X. Ottenwaelder, and T.D.P. Stack Chem. Rev. 104 2004 1013
12. C. Zhang, and N. Jiao J. Am. Chem. Soc. 132 2010 28
13. H. Wang, Y. Wang, C. Peng, J. Zhang, and Q. Zhu J. Am. Chem. Soc. 132 2010 13217
14. S. Chiba, L. Zhang, and J.-Y. Lee J. Am. Chem. Soc. 132 2010 7266
15. K.K. Toh, Y.-F. Wang, E.P.J. Ng, and S. Chiba J. Am. Chem. Soc. 133 2011 13942
16. Y.-F. Wang, H. Chen, X. Zhu, and S. Chiba J. Am. Chem. Soc. 134 2012 11980
17. D. Chandra Mohan, S.N. Rao, and S. Adimurthy J. Org. Chem. 78 2013 1266
18. T. Ohshima, M. Sodeoka, and M. Shibasaki Tetrahedron Lett. 34 1993 8509
19. S. Tategami, T. Yamada, H. Nishino, and K. Kurosawa Tetrahedron Lett. 31 1990 6371
20. C. Zhang, Z. Xu, T. Shen, G. Wu, L. Zhang, and N. Jiao Org. Lett. 14 2012 2362
21. S.O. Kim, C.V. Sastri, M.S. Seo, J. Kim, and W. Nam J. Am. Chem. Soc. 127 2005 4178
22. B. Li, A.-H. Liu, L.-N. He, Z.-Z. Yang, J. Gao, and K.-H. Chen Green Chem. 14 2012 130
23. K. Hasan, N. Brown, and C.M. Kozak Green Chem. 13 2011 1230
24. For recent reviews, see: Organometallic Radical Processes; Trogler, W. C., Ed.; Elsevier: Amsterdam, 1990, Chap. 3, 4, 9, 10.
25. D. Astruc Acc. Chem. Res. 24 1991 36
26. Electron Transfer and Radical Processes in Transition-Metal Chemistry; Astruc, D., Ed.; VCH: New York, 1995, Chap. 3, 5, 6.
27. K.E. Torraca, and L. McElwee-White Coord. Chem. Rev. 206-207 2000 469
28. J.M.R. Narayanam, and C.R.J. Stephenson Chem. Soc. Rev. 40 2011 102
29. B.C. Giglio, V.A. Schmidt, and E.J. Alexanian J. Am. Chem. Soc. 133 2011 13320
30. H. Wang, Y. Wang, D. Liang, L. Liu, J. Zhang, and Q. Zhu Angew. Chem., Int. Ed. 50 2011 5678
31. Z.-Q. Wang, W.-W. Zhang, L.-B. Gong, R.-Y. Tang, X.-H. Yang, Y. Liu, and J.-H. Li Angew. Chem., Int. Ed. 50 2011 8968
32. W. Wei, and J.-X. Ji Angew. Chem., Int. Ed. 50 2011 9097
33. W. Wei, C. Liu, D. Yang, J. Wen, J. You, Y. Suo, and H. Wang Chem. Commun. 2013 10239
34. A. Deb, S. Manna, A. Modak, T. Patra, S. Maity, and D. Maiti Angew. Chem., Int. Ed. 52 2013 9747
35. Y. Su, X. Sun, G. Wu, and N. Jiao Angew. Chem., Int. Ed. 52 2013 9808
36. Q. Lu, J. Zhang, F. Wei, Y. Qi, H. Wang, Z. Liu, and A.W. Lei Angew. Chem., Int. Ed. 52 2013 7156
37. Q. Lu, J. Zhang, G. Zhao, Y. Qi, H. Wang, and A.W. Lei J. Am. Chem. Soc. 135 2013 11481
38. A. Kariya, T. Yamaguchi, T. Nobuta, N. Tada, T. Miura, and A. Itoh RSC Adv. 4 2014 13191
39. R. Chawla, A.K. Singh, and L.D.S. Yadav Eur. J. Org. Chem. 2014 2032
40. Y.M. Markitanov, V.M. Timoshenko, and Y.G. Shermolovich J. Sulfur Chem. 35 2014 188
41. A.K. Singh, R. Chawla, A. Rai, and L.D.S. Yadav Chem. Commun. 2012 3766
42. R. Chawla, R. Kapoor, A.K. Singh, and L.D.S. Yadav Green Chem. 14 2012 1308
43. A.K. Singh, and L.D.S. Yadav Synthesis 2012 591
44. R. Chawla, A.K. Singh, and L.D.S. Yadav Tetrahedron Lett. 53 2012 3382
45. A.K. Singh, R. Chawla, and L.D.S. Yadav Synthesis 2012 2353
46. R. Chawla, A.K. Singh, and L.D.S. Yadav Tetrahedron 69 2013 1720
47. R. Chawla, A.K. Singh, and L.D.S. Yadav Synlett 2013 1558
48. A.K. Singh, R. Chawla, and L.D.S. Yadav Tetrahedron Lett. 54 2013 5099
49. A.K. Singh, R. Chawla, and L.D.S. Yadav Tetrahedron Lett. 55 2014 2845
50. H. Loghmani-Khouzani, M.P. Poorheravi, M.M.M. Sadeghi, L. Caggiano, and R.F.W. Jackson Tetrahedron 64 2008 7419
51. N. Kamigata, K. Udodaira, and T. Shimizu J. Chem. Soc., Perkin Trans. 1 1997 783
52. J. Xiang, M. Ipek, V. Suri, M. Tam, Y.-Z. Xing, N. Huang, Y.-L. Zhang, J. Tobin, T.S. Mansoura, and J. McKewa Bioorg. Med. Chem. 15 2007 4396
53. G.C. Tsui, Q. Glenadel, C. Lau, and M. Lautens Org. Lett. 13 2011 208
54. J.S. Grossert, S. Sotheeswaran, H.R.W. Dharmaratne, and T.S. Cameron Can. J. Chem. 66 1988 2870
55. G. da Silva, M.R. Hamdan, and J.W. Bozzelli J. Chem. Theory Comput. 5 2009 3185