Chinese Journal of Organic Chemistry >
A Green Method for the Synthesis of Sulfones from Thioethers
Received date: 2020-07-09
Revised date: 2020-07-30
Online published: 2020-08-27
Supported by
the National Natural Science Foundation of China(21672151)
With water as oxygen source, a method for the synthesis of sulfones from thioethers under the action of Selecetfluor TM was designed. The yield can reach 99%. The 18O-labeled methylphenylsulfone was prepared with H2 18O. The conditions of this green method are mild and can reach the grams scale.
Key words: thioethers; SelecetfluorTM; water; sulfone compound
Xiang Fang , Wang Wang , Xueyan Yang , Fanhong Wu . A Green Method for the Synthesis of Sulfones from Thioethers[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 412 -417 . DOI: 10.6023/cjoc202007028
[1] | Devendar P.; Yang G.F. Sulfur Chemistry, Springer, Cham , 2019, pp. 35~78. |
[2] | Waldman A.J.; Ng T.L.; Wang P.; Balskus E.P. Chem. Rev. 2017, 117, 5784. |
[3] | Feng M.; Tang B.; H. Liang, S.H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200. |
[4] | Wang D.; Qian E.W.; Amano H.; Okata K.; Ishihara A.; Kabe T. Appl. Catal. A., 2003, 253, 91. |
[5] | (a) Taguchi M.; Nakagawa T.; Nakashima T.; Kawai T. J. Mater. Chem. 2011, 21, 17425. |
[5] | (b) Takagi Y.; Kunishi T.; Katayama T.; Ishibashi Y.; Miyasaka H.; Morimoto M.; Irie M. Photochem. Photobiol. Sci. 2012, 11, 1661. |
[6] | Zhang J.; Mai Y.; Jiang T.; Wang X.; Chen J.; Zhang L.; Gao M.; Li Y. CN 108586297, 2018. |
[7] | Gayakwad E.M.; Patil V.V.; Shankarling G.S. New J. Chem. 2016, 40, 223. |
[8] | Zaburdaeva E.; Dodonov V.; Stepovik L.; Kapuskina I. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1521. |
[9] | Lutz M.; Wenzler M.; Likhotvorik I. Synthesis 2018, 50, 2231. |
[10] | (a) Zheng S.; Huang W.; Gao N.; Cui R.; Zhang M.; Zhao X. Chem. Commun. 2011, 47, 6969. |
[10] | (b) Zhang M.; Zhao M.; Zheng P.; Zhang H.; Zhao X. J. Fluorine Chem. 2016, 189, 13. |
[10] | (c) Gao N.; Zheng S.; Yang W.; Zhao X. Org. Lett. 2011, 13,1514. |
[10] | (d) Gao N.; Guo X.; Zheng S.-C.; Yang W.-K.; Zhao X.-M. Tetrahedron 2012, 68, 9413. |
[11] | Lu J.; Wang Y.; Ma X.; Niu Y.; Singh V.; Ma P.; Zhang C.; Niu J.; Wang J. Dalton Trans. 2018, 47, 8070. |
[12] | Koo D.H.; Kim M.; Chang S. Org. Lett. 2005, 7, 5015. |
[13] | Ali M.H.; Olesen B.; Ranu B.; Clippard L.; Heath J.; Meyer G.; Williams T. Synthesis 2016, 48, 429. |
[14] | Yamazaki S. Bull. Chem. Soc. Jpn. 1996, 69, 2955. |
[15] | Mohammadpoor-Baltork I.; Hill M.; Caggiano L.; Jackson R.F.W. Synlett 2006, 3540. |
[16] | Jeyakumar K.; Chand D.K. Tetrahedron Lett. 2006, 47, 4573. |
[17] | (a) Fuchigami T.; Inagi S. Acc. Chem. Res. 2020, 53, 322. |
[17] | (b) Nyffeler P.T.; Duron S.G.; Burkart M.D.; Vincent S.P.; Wong C.-H. Angew. Chem., Int. Ed. 20 05, 44, 192. |
[18] | Vincent S.P.; Burkart M.D.; Tsai C.-Y.; Zhang Z.; Wong C.-H. J. Org. Chem. 1999, 64, 5264. |
[19] | Kirihara M.; Naito S.; Ishizuka Y.; Hanai H.; Noguchi T. Tetrahedron Lett. 2011, 52, 3086. |
[20] | Hu J.; Yang Y.; Lou Z.; Ni C.; Hu J. Chin. J. Chem. 2018, 36, 1202. |
[21] | Bian M.; Xu F.; Ma C. Synthesis 2007, 2951. |
[22] | Cheng Z.; Sun P.; Tang A.; Jin W.; Liu C. Org. Lett. 2019, 21, 8925. |
[23] | Supale A.R.; Gokavi G.S. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 725. |
[24] | Yang C.; Jin Q.; Zhang H.; Liao J.; Zhu J.; Yu B.; Deng J. Green Chem. 2009, 11, 1401. |
[25] | Hanson P.; Hendrickx R.A.A. J.; Smith, J.R.L. Org. Biomol. Chem. 2008, 6, 745. |
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