CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction

2019/06/13 by Joseph S. Capani, John E. Cochran, Jianglin (Colin) Liang +1 · 4 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Alkyne #Catalysis #Catalytic Cross-Coupling Reactions #Chemical Synthesis and Analysis #Chemistry #Combinatorial chemistry #Functional group #In situ #Organic chemistry #Organoboron and organosilicon chemistry #Palladium #Sonogashira coupling

paper · doi:10.1021/acs.joc.9b01307

openalex publication_date 2019/06/13 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

A practical and mild set of conditions for the Sonogashira reaction utilizing CsF-mediated in situ TMS-alkyne desilylation followed by Sonogashira coupling has been developed for the synthesis of a variety of alkynyl benzenes and heteroarenes in good to excellent yields. This methodology demonstrates excellent functional group tolerance and simple purification, which allows large-scale industrial applications. This one-pot protocol enables a high-yielding Sonogashira coupling with volatile alkynes by avoiding challenging isolation of free alkynes.

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