Visible‐Light‐Mediated Metal‐Free Synthesis of Trifluoromethylselenolated Arenes

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-09, Vol.57 (36), p.11781-11785
Main Authors: Ghiazza, Clément, Debrauwer, Vincent, Monnereau, Cyrille, Khrouz, Lhoussain, Médebielle, Maurice, Billard, Thierry, Tlili, Anis
Format: Article
Language:English
Subjects:
Additives
Aromatic compounds
Catalysis
Chemical Sciences
Inorganic chemistry
Material chemistry
metal-free reactions
Metals
Organic chemistry
Oxidation
photocatalysis
radicals
Reaction mechanisms
Reagents
Salts
Spectroscopy
Synthesis
Temperature requirements
trifluoromethylselenolation
visible light
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Summary: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. Light can make it: Visible‐light‐mediated synthesis of trifluoromethylselenolated arenes under metal‐free conditions is reported. The reaction scope encompasses a large panel of functional groups. Moreover, mechanistic investigations indicate the involvement of a trifluoromethylselenyl radical.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201806165