Abstract
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.
Highlights
The first light-driven method for the α-trifluoromethoxylation of ketones is reported
Among the rapidly emerging perfluorinated groups whose introduction into organic structures is of great interest, the OCF3 moiety occupies a very special place
It should be pointed out that for these 14 commercial molecules the OCF3 is always attached to an aromatic ring
Summary
Lee, E.; Ritter, T. Silver-Mediated Trifluoromethoxylation of Aryl Stannanes and Arylboronic Acids. J. Am. Chem. Soc. 2011, 133, 13308−13310. (b) Guo, S.; Cong, F.; Guo, R.; Wang, L.; Tang, P. Asymmetric Silver-Catalysed Intermolecular Bromotrifluoromethoxylation of Alkenes with a New Trifluoromethoxylation Reagent. Nat.
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