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Palladium-Catalyzed Decarbonylative Sonogashira Coupling of Terminal Alkynes with Carboxylic Acids

Xinyi Li, Long Liu, Tianzeng Huang, Zhi Tang, Chunya Li, Wenhui Li, Tao Zhang, Zhaohui Li, Tieqiao Chen

2021Organic Letters46 citationsDOI

Abstract

A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.

Topics & Concepts

Sonogashira couplingChemistryPalladiumCatalysisTerminal (telecommunication)Combinatorial chemistryCarboxylic acidAlkyneOrganic chemistryTelecommunicationsComputer scienceCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions