Engaging sulfinate salts <i>via</i> Ni/photoredox dual catalysis enables facile C_sp2–SO₂R coupling

Abstract

This report details the development and implementation of a strategy to construct aryl- and heteroaryl sulfones <i>via</i> Ni/photoredox dual catalysis. Using aryl sulfinate salts, the C-S bond can be forged at room temperature under base-free conditions. An array of aryl- and heteroaryl halides are compatible with this approach. The broad tolerance and mild nature of the described reaction could potentially be employed to prepare sulfones with biological relevance (<i>e.g.</i>, in bioconjugation, drug substance synthesis, <i>etc.</i>) as demonstrated in the synthesis of drug-like compounds or their precursors. When paired with existing Ni/photoredox chemistry for C_sp³ -C_sp² cross-coupling, an array of diverse sulfone scaffolds can be readily assembled from bifunctional electrophiles. A mechanistic manifold consistent with experimental and computational data is presented.