Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2–SO2R coupling. Issue 12 (1st March 2018)

• Record Type: Journal Article
• Authors: Cabrera-Afonso, María Jesús; Lu, Zhi-Peng; Kelly, Christopher B.; Lang, Simon B.; Dykstra, Ryan; Gutierrez, Osvaldo; Molander, Gary A.
• Is Part Of: Chemical science. Volume 9:Issue 12(2018)
• Page Start: 3186
• Page End: 3191
• Publication Date: 2018-03-01
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc05402e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A new, mild, functional-group tolerant approach to the construction aryl- and heteroaryl sulfones via Ni/photoredox dual catalysis is described. Abstract : 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 Csp 3 –Csp 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.