Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 1, Pages 409-412Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610210
Keywords
Friedel-Crafts reaction; metal-free conditions; sulfinylation; sulfoxide; visible light
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Funding
- German Science Foundation [GRK 1626]
- Fonds der Chemischen Industrie
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Heteroaromatic sulfoxides are a frequent structural motif in natural products, drugs, catalysts, and materials. We report a metal-free visible-light-accelerated synthesis of heter-oaromatic sulfoxides from sulfinamides and peroxodisulfate. The reaction proceeds at room temperature with blue-light irradiation and allows the C-H sulfinylation of electron-rich heteroarenes, such as pyrroles and indoles. An electrophilic aromatic substitution mechanism is proposed based on the substrate scope, substitution selectivity, and competition experiments with different nucleophiles.
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