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α-Heteroarylation of Thioethers via Photoredox and Weak Brønsted Base Catalysis.
- Source :
-
Organic letters [Org Lett] 2021 Aug 06; Vol. 23 (15), pp. 6115-6120. Date of Electronic Publication: 2021 Jul 23. - Publication Year :
- 2021
-
Abstract
- 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 Brønsted 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.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 23
- Issue :
- 15
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 34297584
- Full Text :
- https://doi.org/10.1021/acs.orglett.1c02151