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Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.

ABSTRACT: [reactions: see text] A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by ICl, I2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.

SUBMITTER: Zhang X

PROVIDER: S-EPMC2532853 | biostudies-literature | 2006 Jan

REPOSITORIES: biostudies-literature

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Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.

Zhang Xiaoxia X Sarkar Sampa S Larock Richard C RC

The Journal of organic chemistry 20060101 1

[reactions: see text] A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by ICl, I2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis o ...[more]

PMID: 16388642

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