Photocatalytic Fluorosulfonylmethylation/Fluorosulfonylation of 2-Amino Aryl Ethynes to Access Dibenzazepine-/Dioxodibenzothiazepine-Functionalized Allyl/Vinyl Sulfonyl Fluorides.

Abstract

This study reports a simple and efficient photocatalytic radical cascade cyclization strategy for the one-step synthesis of allyl- and vinyl-sulfonyl fluorides bearing dibenzazepine or dioxodibenzothiazepine scaffolds. In contrast to the existing synthesis methods of allyl sulfonyl fluoride, this approach employs aryl-terminal alkynes as starting materials, thereby avoiding the reliance on preformed allylic frameworks. The reaction utilizes inexpensive and readily accessible -CH2SO2F and -SO2F precursors, exhibits a broad substrate scope, proceeds under mild conditions, and delivers high stereoselectivity. The synthetic utility of this methodology was further demonstrated through SuFEx-based ligation with other molecules.