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Extended π-Conjugated Structures via Dehydrative C–C Coupling

Cite this: J. Am. Chem. Soc. 2018, 140, 51, 17962–17967
Publication Date (Web):December 14, 2018
https://doi.org/10.1021/jacs.8b09337
Copyright © 2018 American Chemical Society
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    Abstract

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    We describe a methodology for the synthesis of extended aromatic structures through dehydrative C–C coupling from readily accessible diols. Treatment of the diols with a Brønsted acid (para-toluenesulfonic acid) induces the nucleophilic addition of an arene or heteroarene, yielding fully aromatic products in high to quantitative yields with thiophenes, furan, indole, and N,N-dimethylaniline as coupling partners. The C–C coupling reactions proceed under mild, open flask conditions and offer high atom economy, while providing an attractive alternative approach to metal-catalyzed cross-coupling.

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    This article is cited by 12 publications.

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