Sulfoxide Reduction/C(sp³)-S Metathesis Cascade in Ionic Liquid

Chenjing Liu, Dengfeng Chen, Yuanyuan Fu, Fei Wang, Jinyue Luo* and Shenlin Huang*

*College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China, Email: luojinyuenjfu.edu.cn, shuangnjfu.edu.cn

C. Liu, D. Chen, Y. Fu, F. Wang, J. Luo, S. Huang, Org. Lett., 2020, 22, 5701-5705.

DOI: 10.1021/acs.orglett.0c02089

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Abstract

A sulfoxide reduction/C-S bond metathesis cascade between sulfoxides and alkyl bromides in an ionic liquid provides high-value sulfides without the use of any catalysts or bases. In this cascade, classical Kornblum oxidation is employed to reduce sulfoxides with alkyl bromides. This protocol features high functional tolerance, mild conditions, promising scalability, and a sustainable solvent.

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proposed mechanism

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Key Words

reduction of sulfoxides, synthesis of sulfides, ionic liquids

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ID: J54-Y2020