Engaging sulfinate salts Ni/photoredox dual catalysis enables facile C-SOR coupling

• Published in: Chemical science (Cambridge) 2018-03, Vol.9 (12), p.3186-3191
• Main Authors: Cabrera-Afonso, María Jesús, Lu, Zhi-Peng, Kelly, Christopher B, Lang, Simon B, Dykstra, Ryan, Gutierrez, Osvaldo, Molander, Gary A
• Format: Article
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c7sc05402e

This report details the development and implementation of a strategy to construct aryl- and heteroaryl sulfones via 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 ( e.g. , in bioconjugation, drug substance synthesis, etc. ) as demonstrated in the synthesis of drug-like compounds or their precursors. When paired with existing Ni/photoredox chemistry for C sp 3 -C sp 2 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. A new, mild, functional-group tolerant approach to the construction aryl- and heteroaryl sulfones via Ni/photoredox dual catalysis is described.