Synthesis of 2, 3-disubstituted benzo [b] furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization

D Yue, T Yao, RC Larock

Index: Yue, Dawei; Yao, Tuanli; Larock, Richard C. Journal of Organic Chemistry, 2005 , vol. 70, # 25 p. 10292 - 10296

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Citation Number: 256

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.