Issue 71, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
05 Aug 2018
Accepted
11 Aug 2018
First published
20 Aug 2018

Chem. Commun., 2018,54, 9985-9988

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements