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Visible-Light-Mediated Metal-Free Synthesis of Trifluoromethylselenolated Arenes
Clément Ghiazza1, Vincent Debrauwer1, Cyrille Monnereau2
1Institute of Chemistry and Biochemistry (ICBMS-UMR, CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, 43 Bd du 11 Novembre 1918, 69622, Villeurbanne, France.
Abstract:
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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