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Radical α-Trifluoromethoxylation of Ketones under Batch and Flow Conditions by Means of Organic Photoredox Catalysis.


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.

SUBMITTER: Duhail T 

PROVIDER: S-EPMC8453633 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Radical α-Trifluoromethoxylation of Ketones under Batch and Flow Conditions by Means of Organic Photoredox Catalysis.

Duhail Thibaut T   Bortolato Tommaso T   Mateos Javier J   Anselmi Elsa E   Jelier Benson B   Togni Antonio A   Magnier Emmanuel E   Dagousset Guillaume G   Dell'Amico Luca L  

Organic letters 20210901 18


The first light-driven method for the α-trifluoromethoxylation of ketones is reported. Enol carbonates react with <i>N</i>-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 pot  ...[more]

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