1. CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction
- Author
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Jianglin Colin Liang, Cochran John E, and Joseph S Capani
- Subjects
In situ ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Sonogashira coupling ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences - 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.
- Published
- 2019
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