Radical Anion Promoted Chemoselective Cleavage of Csp²-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols

Jixiang Bai, Tianxin Wang, Botao Dai, Qingchao Liu*, Peiyuan Yu* and Tiezheng Jia*

*Northwest University, Taibai North Road 229, Xi'an, Shanxi 710069; SUSTech, 1088 Xueyuan Boulevard, Shenzhen, Guangdong 518055, P.R. China, Email: liuqc21nwu.edu.cn, yupysustech.edu.cn, jiatzsustech.edu.cn

J. Bai, T. Wang, B. Dai, Q. Liu, P. Yu, T. Jia, Org. Lett., 2021, 23, 5761-5765.

DOI: 10.1021/acs.orglett.1c01926

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Abstract

A formal cross-coupling of aryl methyl sulfones and alcohols affords alkyl aryl ethers via an S_RN1 pathway. A dimsyl-anion initiated radical chain process was revealed as the major pathway.

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Key Words

aryl ethers

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ID: J54-Y2021