Access to Terminal Alkynes via Palladium-Catalyzed Coupling of ArCl with a Low Catalyst Loading of 0.08 mol %

The synthesis of terminal alkynes from inexpensive aryl chlorides remains a challenging task in organic synthesis. Here, a Heck-Cassar reaction of aryl chlorides with (triisopropylsilyl)acetylene catalyzed by low loadings of palladium (0.08 mol %) has been developed. Through subsequent desilylation, aryl-substituted terminal alkynes can be readily prepared. This reaction features robustness and good functional group compatibility, making it suitable for the late-stage modification of drug molecules.