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Photoinduced Copper-Catalyzed Site-Selective C(sp<sup>2</sup>)–C(sp) Cross-Coupling via Aryl Sulfonium Salts

Lei Liang, Hong‐Ying Niu, Renlong Li, Yao-Fei Wang, Jin-Kai Yan, Chang-Gong Li, Hai‐Ming Guo

2020Organic Letters61 citationsDOI

Abstract

The classical Sonogashira reaction of aryl electrophiles in the presence of Pd catalysts has been well established as a potent method for arylalkyne synthesis. However, the site-selective C(sp2)–C(sp) cross-coupling strategy using a non-noble-metal catalyst is rare. An efficient alternative approach for the synthesis of arylalkynes via a Cu-catalyzed Sonogashira-type reaction promoted by visible light is described. This method enables site-selective alkynylation from aryl sulfonium salts derived from diverse arenes to a set of arylalkynes with high selectivity and high functional-group compatibility. Moreover, rapid alkynylation of drug molecules is demonstrated.

Topics & Concepts

SulfoniumChemistrySonogashira couplingArylCatalysisCombinatorial chemistryElectrophileTrifluoromethanesulfonateSelectivityCoupling reactionAlkynylationOrganic chemistryPalladiumSalt (chemistry)AlkylSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
Photoinduced Copper-Catalyzed Site-Selective C(sp<sup>2</sup>)–C(sp) Cross-Coupling via Aryl Sulfonium Salts | Litcius