Boosting Sulfonylation Reactions between Vinyl Triflates and Alkenes toward β-Ketosulfones Using Aqueous Sulfurous Acid

Takuji Kawamoto; Yuki Takeda; Takahiro Kawabata; Akio Kamimura

doi:10.1055/a-2295-8117

Synthesis, Table of Contents

Synthesis 2024; 56(21): 3334-3340
DOI: 10.1055/a-2295-8117

paper

Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)

Boosting Sulfonylation Reactions between Vinyl Triflates and Alkenes toward β-Ketosulfones Using Aqueous Sulfurous Acid

Takuji Kawamoto∗

,

Yuki Takeda

,

Takahiro Kawabata

,

Akio Kamimura

Abstract

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Abstract

We successfully synthesized trifluoromethylated β-ketosulfones via the reaction of vinyl triflates with alkenes employing aqueous sulfurous acid as an external source of SO₂. The PhSSPh/photoinitiated reaction with vinyl triflates that contain electron-deficient groups or halogens did not show any base-related effects, whereas the radical reaction was impeded in the absence of a base in the case of vinyl triflates generated from phenylacetylenes.

Key words

radicals - trifluoromethylation - sulfonylation - vinyl triflates - β-ketosulfones - sulfurous acid

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References

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Supplementary Material

Supporting Information