Shining light for organophotocatalysed site-selective sulfonylation of anilides

Abstract

The site-selective sulfonylation of C(sp²)–H bonds of anilide and quinoline amide derivatives has been developed using organophotocatalysis. This mild and sustainable protocol, which operates at room temperature, precludes the requirement for any metal-based catalyst or photocatalyst and oxidant, which are the challenges associated with existing methodologies. Furthermore, the generation of aryl sulfonyl radicals from commercially available aryl sulfonyl chlorides has been achieved through the use of Rose Bengal as an organophotocatalyst, an approach that was previously unexplored. The detailed mechanistic investigation unveiled the underlying mechanism for site-selective sulfonylation at both the proximal and distal positions, thereby establishing a straightforward approach for building valuable aryl sulfone scaffolds.