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Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction

Dmitri Gelman, Stephen L. Buchwald*

*Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Email:

D. Gelman, S. L. Buchwald, Angew. Chem. Int. Ed., 2003, 42, 5993-5996.

DOI: 10.1002/anie.200353015 (free Supporting Information)


General protocols for the palladium-catalyzed coupling of aryl chlorides and alkynes and aryl tosylates and alkynes were developed. Addition of a copper cocatalyst can inhibit product formation. In the case of highly active catalysts, screening for new catalyst systems need to be carried out both in the presence and absence of copper.

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Key Words

alkynes, aryl chlorides, C-C coupling, cross-coupling, palladium, Sonogashira Coupling

ID: J06-Y2003-1050