Palladium-Catalyzed Desulfonative Carbonylation of Thiosulfonates: Elimination of SO₂ and Insertion of CO

Jian-Xing Xu, Le-Cheng Wang and Xiao-Feng Wu*

*Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Science, 116023 Dalian, Liaoning, China, Email: xwu2020dicp.ac.cn

J.-X. Xu, L.-C. Wang, X.-F. Wu, Org. Lett., 2022, 24, 4820-4824.

DOI: 10.1021/acs.orglett.2c01951

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Abstract

A palladium-catalyzed desulfonative carbonylation of S-aryl/alkyl benzenesulfonothioates provides thioesters in good yields by SO₂ extrusion and CO insertion under 1 bar of CO. Dimethylacetamide (DMAc) as solvent facilitated this desulfonative carbonylation due to its high absorbing ability of SO₂.

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proposed mechanism

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Key Words

thioesters, arenes

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ID: J54-Y2022