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Photoinduced Pd‐Catalyzed Direct Sulfonylation of Allylic C−H Bonds

Kallol Mukherjee, Kelvin Pak Shing Cheung, Vladimir Gevorgyan

2024Angewandte Chemie International Edition35 citationsDOIOpen Access PDF

Abstract

Allylic sulfones are valuable motifs due to their medicinal and biological significance and their versatile chemical reactivities. While direct allylic C-H sulfonylation represents a straightforward and desirable approach, these methods are primarily restricted to terminal alkenes, leaving the engagement of the internal counterparts a formidable challenge. Herein we report a photocatalytic approach that accommodates both cyclic and acyclic internal alkenes with diverse substitution patterns and electronic properties. Importantly, the obtained allylic sulfones can be readily diversified into a wide range of products, thus enabling formal alkene transposition and all-carbon quaternary center formation through the sequential C-H functionalization.

Topics & Concepts

Allylic rearrangementCatalysisPalladiumChemistryMedicinal chemistryOrganic chemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions
Photoinduced Pd‐Catalyzed Direct Sulfonylation of Allylic C−H Bonds | Litcius