83782-26-7Relevant articles and documents
α-Heteroarylation of Thioethers via Photoredox and Weak Br?nsted Base Catalysis
Alfonzo, Edwin,Hande, Sudhir M.
supporting information, p. 6115 - 6120 (2021/08/16)
We report the C-H activation of thioethers to α-thio alkyl radicals and their addition to N-methoxyheteroarenium salts for the redox-neutral synthesis of α-heteroaromatic thioethers. Studies are consistent with a two-step activation mechanism, where oxidation of thioethers to sulfide radical cations by a photoredox catalyst is followed by α-C-H deprotonation by a weak Br?nsted base catalyst to afford α-thio alkyl radicals. Further, N-methoxyheteroarenium salts play additional roles as a source of methoxyl radical that contributes to α-thio alkyl radical generation and a sacrificial oxidant that regenerates the photoredox catalytic cycle.
