Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts

Fu-Sheng He*, Ping Bao, Zhimei Tang, Feiyan Yu, Wei-Ping Deng and Jie Wu*

*School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, Jiaojiang 318000, Zhejiang, China, Email: jie_wufudan.edu.cn

F.-S. He, P. Bao, Z. Zang, F. Yu, W.-P. Deng, J. Wu, Org. Lett., 2022, 24, 2955-2960.

DOI: 110.1021/acs.orglett.2c01132

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Abstract

A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO₂)₂ and thianthrenium salts provides diverse β-keto sulfones in moderate yields with good functional group compatibility. The use of a MeOH-derived methyl thianthrenium intermediate enables the synthesis of α-methylsulfonated ketones.

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proposed mechanism

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Key Words

sulfones, photochemistry, multicomponent reactions

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ID: J54-Y2022