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

Joseph S. Capani Jr., John E. Cochran, Jianglin (Colin) Liang*

*Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States, Email: colin_liangvrtx.com

J. S. Capani Jr., J. E. Cochran, J. Liang, J. Org. Chem., 2019, 84, 9378-9384.

DOI: 10.1021/acs.joc.9b01307



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Abstract

A CsF-mediated in situ TMS-alkyne desilylation followed by Sonogashira coupling enables the synthesis of various alkynyl benzenes and heteroarenes in good yields. This methodology offers excellent functional group tolerance and simple purification, which allows large-scale applications, and avoids the challenging isolation of volatile free alkynes.

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Key Words

Sonogashira Coupling, Alkynylation


ID: J42-Y2019