Merging Copper(I) Photoredox Catalysis and Iodine(III) Chemistry for the Oxy-monofluoromethylation of Alkenes |
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Authors: | Nagarajan Ramkumar Larisa Baumane Dzintars Zacs Janis Veliks |
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Institution: | 1. Latvian Institute of Organic Synthesis, Aizkraukles iela 21, LV-1006 Riga, Latvia;2. Institute of Food Safety, Animal Health and Environment “BIOR”, Lejupes iela 3, LV-1076 Riga, Latvia |
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Abstract: | A simple process for the oxy-monofluoromethylation of alkenes is described. In combination with visible-light copper(I) photoredox catalysis, an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands serves as a powerful source of a monofluoromethyl (CH2F) radical, enabling the step economical synthesis of γ-fluoro-acetates from a broad range of olefinic substrates under mild conditions. Applications to late-stage diversification of alkenes derived from complex molecules, amino acids and the synthesis of fluoromethylated heterocycles are also demonstrated. |
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Keywords: | Copper Hypervalent Iodine Monofluoromethylation Photoredox Catalysis Radicals |
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