Issue 41, 2022

One-pot ester and thioester formation mediated by pentafluoropyridine (PFP)

Abstract

Acyl fluorides are valuable synthetic intermediates, but in some cases they can be challenging to handle and difficult to isolate given their susceptibility to degradation. In addition, many reagents utilised to prepare acyl fluorides are incompatible with in situ generation strategies and require the acyl fluoride to be isolated before any further reaction can take place. The combination of these factors has meant that acyl fluorides are currently under investigated in nucleophilic substitution processes, and often only a limited substrate scope is tolerated where they have been used. Herein, we report that pentafluoropyridine can be utilised to generate acyl fluorides in situ under mild conditions, and that they can subsequently be used to generate a range of esters and thioesters. This methodology offers a simple one-pot synthesis of esters and thioesters directly from parent carboxylic acids.

Graphical abstract: One-pot ester and thioester formation mediated by pentafluoropyridine (PFP)

Supplementary files

Article information

Article type
Paper
Submitted
15 Jul 2022
Accepted
23 Aug 2022
First published
23 Aug 2022
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2022,20, 8059-8064

One-pot ester and thioester formation mediated by pentafluoropyridine (PFP)

L. N. D. Beardmore, S. L. Cobb and W. D. G. Brittain, Org. Biomol. Chem., 2022, 20, 8059 DOI: 10.1039/D2OB01268E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements