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Chemodivergent Synthesis of Allylic Sulfones via Ligand-Controlled Coupling of Allenes with Sulfinic Acids

Jiahao Zeng, Dingchang Li, Sheng Zhang, Zhuang‐Ping Zhan

2022Organic Letters22 citationsDOI

Abstract

Allylic sulfones are important building blocks in organic synthesis and pharmaceutical chemistry. Herein, we disclose a chemodivergent protocol for Pd-catalyzed and ligand-controlled coupling of allenes with sulfinic acids, providing straightforward and atom-economical access to branched allylic sulfones and linear allylic sulfones bearing a conjugated (Z,E)-1,3-diene scaffold in good yields with high selectivities. This strategy features mild conditions, an unprecedented substrate scope, and functional group compatibility.

Topics & Concepts

Allylic rearrangementChemistrySulfinic acidLigand (biochemistry)Combinatorial chemistryFunctional groupCatalysisDieneOrganic chemistryReceptorNatural rubberBiochemistryPolymerSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis of Indole Derivatives