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Visible‐Light‐Mediated Metal‐Free Synthesis of Trifluoromethylselenolated Arenes
Authors:Clément Ghiazza  Vincent Debrauwer  Dr. Cyrille Monnereau  Lhoussain Khrouz  Dr. Maurice Médebielle  Dr. Thierry Billard  Dr. Anis Tlili
Affiliation:1. http://www.FMI‐Lyon.fr 0000-0002-1264-2559 Institute of Chemistry and Biochemistry (ICBMS-UMR, CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, Villeurbanne, France;2. Institute of Chemistry and Biochemistry (ICBMS-UMR, CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, Villeurbanne, France;3. Univ Lyon, Ens de Lyon, CNRS UMR 5182, Université Lyon 1, Laboratoire de Chimie, Lyon, France;4. CERMEP—in vivo imaging, Groupement Hospitalier Est, Lyon, 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.
Keywords:metal-free reactions  photocatalysis  radicals  trifluoromethylselenolation  visible light
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