Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates

Abstract

We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluorosulfates through a free fluorosulfonyl radical (FSO₂˙). This methodology provides a facile approach to aromatic β-keto sulfonyl fluorides, featuring sustainable conditions and a broad substrate scope (32 examples) with 33%–90% isolated yields.