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

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

Publication History

Received: 31 January 2024

Accepted after revision: 27 March 2024

Accepted Manuscript online:
27 March 2024

Article published online:
25 April 2024

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