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Synthesis of 2,3-Disubstituted Benzo[b]furans by the Palladium-Catalyzed Coupling of o-Iodoanisoles and Terminal Alkynes, Followed by Electrophilic Cyclization

Dawei Yue, Tuanli Yao and Richard C. Larock*

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, Email: larockiastate.edu

D. Yue, T. Yao, R. C. Larock, J. Org. Chem., 2005, 70, 10292-10296.

DOI: 10.1021/jo051299c (free Supporting Information)


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Abstract

2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the Sonogashira coupling of various o-iodoanisoles and terminal alkynes, followed by an electrophilic cyclization. Aryl- and vinylic-substituted alkynes give cyclization products in excellent yields.

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Key Words

Benzo[b]furans


ID: J42-Y2005-2090