Photoredox‐Catalyzed Selective Synthesis of Allylic Perfluoroalkanes from Alkenes
| Autor: | Emmanuel Magnier, Flavien Bourdreux, Guillaume Dagousset, Anne-Laure Barthelemy |
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| Přispěvatelé: | Institut Lavoisier de Versailles (ILV), Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique, CNRS, A.L.B. thanks the French Ministry of Research for a doctoral fellowship. Youssef El-Ahmad and Victor Certal (Sanofi Vitry sur Seine) are acknowledged for stimulating scientific discussions and French Fluorine Network (CNRS GIS Fluor) for support., Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2020 |
| Předmět: |
Reaction conditions
Allylic rearrangement Trifluoromethyl [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry photoredox catalysis Radical Organic Chemistry Iminium Photoredox catalysis allylic trifluoromethylation General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Styrene sulfilimino iminium chemistry.chemical_compound chemistry [CHIM]Chemical Sciences perfluoroalkyl radicals visible light |
| Zdroj: | Chemistry-A European Journal Chemistry-A European Journal, Wiley-VCH Verlag, 2020, 26 (45), pp.10213-10216. ⟨10.1002/chem.202002046⟩ |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | International audience; We report herein a novel photoredox-catalyzed synthesis of allylic trifluoromethanes. The use of sulfilimino iminium as a source of trifluoromethyl radicals proves crucial to achieving high selectivity. Importantly, both styrene derivatives and unactivated alkenes are for the first time suitable partners for this process. The mild reaction conditions are compatible with a variety of functional groups. Remarkably, this method is readily broadened to other perfluoroalkyl groups (RF=CFCl2, CF2Br, C4F9). An extensive mechanistic study is also provided. |
| Databáze: | OpenAIRE |
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