Radical α-Trifluoromethoxylation of Ketones under Batch and Flow Conditions by Means of Organic Photoredox Catalysis
| Autor: | Emmanuel Magnier, Elsa Anselmi, Tommaso Bortolato, Thibaut Duhail, Luca Dell'Amico, Benson J. Jelier, Guillaume Dagousset, Javier Mateos, Antonio Togni |
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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), Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Eidgenössische Technische Hochschule - Swiss Federal Institute of Technology [Zürich] (ETH Zürich) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Letter
010405 organic chemistry Chemistry Organic Chemistry Photoredox catalysis 010402 general chemistry 01 natural sciences Biochemistry Enol 0104 chemical sciences Catalysis chemistry.chemical_compound Flow conditions Yield (chemistry) [CHIM]Chemical Sciences Organic chemistry Physical and Theoretical Chemistry Chemoselectivity ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Organic Letters, 23 (18) Organic Letters Organic Letters, American Chemical Society, 2021, 23 (18), pp.7088-7093. ⟨10.1021/acs.orglett.1c02494⟩ |
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.3929/ethz-b-000508248 |
| Popis: | The first light-driven method for the α-trifluoromethoxylation of ketones is reported. Enol carbonates react with N-trifluoromethoxy-4-cyano-pyridinium, using the photoredox catalyst 4-CzIPN under 456 nm irradiation, affording the α-trifluoromethoxy ketones in ≤50% isolated yield and complete chemoselectivity. As shown by 29 examples, the reaction is general and proceeds very rapidly under batch (1 h) and flow conditions (2 min). Diverse product manipulations demonstrate the synthetic potential of the disclosed method in accessing elusive trifluoromethoxylated bioactive ingredients. Organic Letters, 23 (18) ISSN:1523-7060 ISSN:1523-7052 |
| Databáze: | OpenAIRE |
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