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Issue 2, 2017
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One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

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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

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Publication details

The article was received on 01 Sep 2016, accepted on 02 Oct 2016 and first published on 11 Oct 2016


Article type: Edge Article
DOI: 10.1039/C6SC03924C
Citation: Chem. Sci., 2017,8, 1233-1237
  • Open access: Creative Commons BY license
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    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

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