Saturated Heterocyclic Sulfamoyl Fluorides: Building Blocks for the SuFEx Chemistry

Abstract

A scalable protocol for direct SO2F2-based fluorosulfonylation of saturated (hetero)cyclic and functionalized amines is reported. The method is cost-effective and applicable for multigram preparation of structurally diverse compounds, as illustrated by the synthesis of 58 building blocks decorated with common functional groups. A comparison of overall yields of products demonstrates the advantages of the present method over alternative approaches. The obtained functionalized sp3-enriched sulfamoyl fluorides can be considered a new generation of building blocks for SuFEx (sulfur fluoride exchange) chemistry. The synthetic utility of the synthesized building blocks was demonstrated by late-stage reactions tolerating the SO2F functionality as well as transformations to provide the corresponding sulfamide, sulfamate, and sulfonamide derivatives.