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Article

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

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Dawei Yue, Tuanli Yao, and Richard C. Larock*

Department of Chemistry, Iowa State University, Ames, Iowa 50011

J. Org. Chem., 2005, 70 (25), pp 10292–10296

DOI: 10.1021/jo051299c

Publication Date (Web): November 11, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, larock@iastate.edu

Abstract

2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I₂, PhSeCl, or p-O₂NC₆H₄SCl. Aryl- and vinylic-substituted alkynes undergo electrophilic cyclization in excellent yields. Biologically important furopyridines can be prepared by this approach in high yields.

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Published In Issue December 09, 2005
Received June 24, 2005

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Article

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

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Recommend & Share

Related Content

Synthesis of 3-Iodoindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Acetylenes, Followed by Electrophilic Cyclization

An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization

Regio- and Stereoselective Synthesis of Isoindolin-1-ones via Electrophilic Cyclization

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