Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 36, Pages 11781-11785Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806165
Keywords
metal-free reactions; photocatalysis; radicals; trifluoromethylselenolation; visible light
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Funding
- la region Rhone Alpes
- French Fluorine Network
- federation RENARD
- Departement de Chimie Moleculaire, Universite Grenoble Alpes
- CNRS, ICBMS (UMR 5246), ICL (Institut de Chimie de Lyon)
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The first visible-light-mediated synthesis of trifluoromethylselenolated arenes under metal-free conditions is reported. The use of an organic photocatalyst enables the trifluoromethylselenolation of arene diazonium salts using the shelf-stable reagent trifluoromethyl tolueneselenosulfonate at room temperature. The reaction does not require the presence of any additives and shows high functional-group tolerance, covering a very broad range of starting materials. Mechanistic investigations, including EPR spectroscopy, luminescence investigations, and cyclic voltammetry allow rationalization of the reaction mechanism.
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