Journal
ORGANIC LETTERS
Volume 23, Issue 18, Pages 7088-7093Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02494
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Funding
- Agence Nationale de la Recherche (ANR) with PRCI [ANR-17-CE07-0048-01]
- University of Padova [11BIRD2020-UNIPD]
- CariParo Foundation
- Synergy-Progetti di Eccellenza
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A light-driven method for the alpha-trifluoromethoxylation of ketones has been developed, showing good generality and efficiency under batch and flow conditions. The method demonstrates the potential in accessing a variety of elusive trifluoromethoxylated bioactive ingredients.
The first light-driven method for the alpha-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 alpha-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.
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