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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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Supplementary files

Article information


Submitted
05 Aug 2018
Accepted
11 Aug 2018
First published
20 Aug 2018

Chem. Commun., 2018,54, 9985-9988
Article type
Communication

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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