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Ligand-, Copper-, and Amine-Free Sonogashira Reaction of Aryl Iodides and Bromides with Terminal Alkynes

Sameer Urgaonkar and John G. Verkade*

*Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011, Email: jverkadeiastate.edu

S. Urgaonkar, J. G. Verkade, J. Org. Chem., 2004, 69, 5752-5755.

DOI: 10.1021/jo049325e (free Supporting Information)


Abstract

An efficient ligand-, copper-, and amine-free palladium-catalyzed Sonogashira reaction of aryl iodides and bromides with terminal alkynes at room temperature has been developed. The key reagent is tetrabutylammonium acetate as the base. This method tolerates a broad range of functional groups.

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Key Words

Sonogashira Coupling, Alkynylations, Palladium Catalysis


ID: J42-Y2004-650