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Issue 71, 2018
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Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C–H bonds

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Abstract

Acyl fluorides are versatile acylating agents owing to their unique stability. Their synthesis, however, can present challenges and is typically accomplished through deoxyfluorination of carboxylic acids. Here, we demonstrate that acyl fluorides can be prepared directly from aldehydes via a C(sp2)–H fluorination reaction involving the inexpensive photocatalyst sodium decatungstate and electrophilic fluorinating agent N-fluorobenzenesulfonimide. This convenient fluorination strategy enables direct conversion of aliphatic and aromatic aldehydes into acylating agents.

Graphical abstract: Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C–H bonds

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Publication details

The article was received on 05 Aug 2018, accepted on 11 Aug 2018 and first published on 20 Aug 2018


Article type: Communication
DOI: 10.1039/C8CC06375C
Chem. Commun., 2018,54, 9985-9988

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    Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C–H bonds

    M. Meanwell, J. Lehmann, M. Eichenberger, R. E. Martin and R. Britton, Chem. Commun., 2018, 54, 9985
    DOI: 10.1039/C8CC06375C

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