1.1 Sulfonyl Fluorides and Acyl Fluorides

Abstract

Sulfonyl fluorides have numerous applications in both synthetic organic chemistry as fluorinating agents and as precursors to sulfur(VI) moieties, and in chemical biology as covalent inhibitors and chemical probes. The utility of sulfonyl fluorides arises from the properties of the S—F bond, as the high bond strength and polarization imparts stability and chemoselectivity that differentiates this group from other sulfur(VI) halides. Likewise, acyl fluorides have found widespread use in organic synthesis as reactive intermediates. The increased stability toward hydrolysis and aminolysis in comparison to acyl chlorides and bromides are a result of the relative strength and electrostatic stability of the C—F bond. In this review, we provide an overview of synthetic approaches to these valuable motifs, with a focus on versatile and easy-to-handle protocols.

Key words

organofluorine chemistry - sulfonyl fluorides - sulfur(VI) fluorides - acyl fluorides - acid fluorides

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