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

A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO2)2 and thianthrenium salts is achieved, providing diverse β-keto sulfones in moderate to good yields. This protocol features easily accessible starting materials and good functional group compatibility, enabling the introductio...

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Bibliographic Details
Published in:Organic letters 2022-04, Vol.24 (15), p.2955-2960
Main Authors: He, Fu-Sheng, Bao, Ping, Tang, Zhimei, Yu, Feiyan, Deng, Wei-Ping, Wu, Jie
Format: Article
Language:English
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Summary:A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO2)2 and thianthrenium salts is achieved, providing diverse β-keto sulfones in moderate to good yields. This protocol features easily accessible starting materials and good functional group compatibility, enabling the introduction of various functionalized sulfonyl groups into ketones. Furthermore, as one of the important industrial raw materials, methanol can be employed as the methyl source to prepare α-methylsulfonated ketones through a methyl thianthrenium intermediate for the first time.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01132