Meyer, Andreas Uwe and Wimmer, Alexander and Koenig, Burkhard (2017) Visible-Light-Accelerated C-H Sulfinylation of Heteroarenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56 (1). pp. 409-412. ISSN 1433-7851, 1521-3773
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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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PALLADIUM-CATALYZED ARYLATION; TRANSITION-METAL CATALYSIS; ARYL BENZYL SULFOXIDES; SULFENATE ANIONS; ENANTIOENRICHED SULFOXIDES; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC REACTIVITIES; ASYMMETRIC CATALYSIS; PHOTOREDOX CATALYSIS; DIARYL SULFOXIDES; Friedel-Crafts reaction; metal-free conditions; sulfinylation; sulfoxide; visible light |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:01 |
| Last Modified: | 11 Feb 2019 13:01 |
| URI: | https://pred.uni-regensburg.de/id/eprint/578 |
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