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

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Sameer Urgaonkar and John G. Verkade*

Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011 %jverkade@iastate.edu

J. Org. Chem., 2004, 69 (17), pp 5752–5755

DOI: 10.1021/jo049325e

Publication Date (Web): July 16, 2004

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Conditions for an efficient ligand-, copper-, and amine-free palladium-catalyzed Sonogashira reaction of aryl iodides and bromides with terminal alkynes have been developed. Critical to the success of this new protocol is the use of tetrabutylammonium acetate as the base. Noteworthy features of this method are room-temperature conditions and the tolerance of a broad range of functional groups in both reaction partners.

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History

Published In Issue August 20, 2004
Received April 21, 2004

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