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Updated: Jan 4, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers
Artem A Zemtsov1, Salavat S Ashirbaev1, Vitalij V Levin1
1N. D. Zelinsky Institute of Organic Chemistry , Leninsky prosp. 47 , 119991 Moscow , Russian Federation.
Abstract:
A method for the generation of free radicals from thiazolinium salts upon photocatalytic reduction is described. The thiazolinium salts are generated by treatment with methyl triflate of 2-mercaptothiazolines, which can be readily obtained from alkyl bromides and tosylates via a nucleophilic substitution reaction or by hydrothiolation of alkenes. Silyl enol ethers were used to trap the radicals, furnishing ketones after successive single-electron oxidation and elimination of the silyl cation.
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