Extended π‑Conjugated Structures via Dehydrative C–C Coupling

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 pr...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-12, Vol.140 (51), p.17962-17967
Main Authors: Voll, Constantin-Christian A, Swager, Timothy M
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b09337