A simple approach to highly functionalized benzo [b] furans from phenols and aryl iodides via aryl propargyl ethers

…, R Vinodkumar, K Mukkanti, A Thomas, B Gopalan

Index: Lingam, V.S. Prasada Rao; Vinodkumar, Ramanatham; Mukkanti, Khagga; Thomas, Abraham; Gopalan, Balasubramanian Tetrahedron Letters, 2008 , vol. 49, # 27 p. 4260 - 4264

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Citation Number: 24

Abstract

A variety of mono-and disubstituted phenols are alkylated with propargyl bromide to give phenyl 2-propynyl ethers, which were further coupled with aryl iodides under Sonogashira reaction conditions to give 3-phenoxy-1-aryl-1-propyne derivatives. The latter compounds underwent an initial Claisen rearrangement followed by ring closure to give functionalized benzo [b] furans in moderate to good yields.

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