Photoredox Reaction of 2‑Mercaptothiazolinium Salts with Silyl Enol Ethers

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.