Synthesis of 3,4-Disubstituted 2H-Benzopyrans through C-C Bond Formation via Electrophilic Cyclization

Shilpa A. Worlikar, Tanay Kesharwani, Tuanli Yao and Richard C. Larock*

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

S. A. Worlikar, T. Kesharwani, T. Yao, R. C. Larock, J. Org. Chem., 2007, 72, 1347-1353.

DOI: 10.1021/jo062234s

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Abstract

A mild, electrophilic cyclization of substituted propargylic aryl ethers by I₂, ICl, and PhSeBr produces 3,4-disubstituted 2H-benzopyrans in excellent yields. This methodology tolerates various functional groups, such as methoxy, alcohol, aldehyde, and nitro groups.

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Key Words

2H-Chromenes, Vinyl Iodides

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ID: J42-Y2007-0570