Issue 2, 2017

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

Abstract

A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.

Graphical abstract: One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

Supplementary files

Article information

Article type
Edge Article
Submitted
01 sep 2016
Accepted
02 okt 2016
First published
11 okt 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 1233-1237

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

A. T. Davies, J. M. Curto, S. W. Bagley and M. C. Willis, Chem. Sci., 2017, 8, 1233 DOI: 10.1039/C6SC03924C

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.

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