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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.

SUBMITTER: Davies AT

PROVIDER: S-EPMC5369543 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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

Davies Alyn T AT Curto John M JM Bagley Scott W SW Willis Michael C MC

Chemical science 20161011 2

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 p ...[more]

PMID: 28451264

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