Dehydroxylative Sulfonylation of Alcohols

Yi-Jun Xiang, Shun Liu, Jing Zhou, Jin-Hong Lin*, Xu Yao*, and Ji-Chang Xiao*

*Shanghai Institute of Organic Chemistry, 345 Lingling Road, 200032 Shanghai; University of South China, 421001 Hengyang, PR China, Email: jlinshu.edu.cn, 355938360qq.com, jchxiaosioc.ac.cn

Y.-J. Xiang, S.-Liu, J. Zhou, J.-H. Lin, X. Yao, J.-C. Xiao, J. Org. Chem., 2023, 88, 4818-4828.

DOI: 10.1021/acs.joc.2c03085

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Abstract

The combination of Ph₃P/ICH₂CH₂I promotes a dehydroxylative sulfonylation of benzylic and allylic alcohols with a variety of sulfinates in short reaction time. Using Ph₂PMe and elevated temperatures, the protocol can be extended to alkyl alcohols. Various sulfonyl groups can be incorporated, such as CF₃SO₂ and HCF₂SO₂, which are fluorinated groups of interest in pharmaceutical chemistry.

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proposed mechanism

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Key Words

allyl sulfones, propargyl sulfones, alkyl sulfones

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ID: J42-Y2023