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Synthesis of 3,4-Disubstituted 2 H -Benzopyrans through C−C Bond Formation via Electrophilic Cyclization
Journal article   Peer reviewed

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

Shilpa A. Worlikar, Tanay Kesharwani, Tuanli Yao and Richard C. Larock
Journal of organic chemistry, Vol.72(4), pp.1347-1353
02/01/2007
PMCID: PMC2527782
PMID: 17288382
Web of Science ID: WOS:000244071100036

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Abstract

The electrophilic cyclization of substituted propargylic aryl ethers by I2, ICl, and PhSeBr produces 3,4-disubstituted 2H-benzopyrans in excellent yields. This methodology results in vinylic halides or selenides under mild reaction conditions and tolerates a variety of functional groups, including methoxy, alcohol, aldehyde, and nitro groups.

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