Extended conjugated structures are ubiquitously represented in the field of organic materials because of their favorable optical and electronic properties. Many of these structures are synthesized by transition-metal cross-coupling reactions. We describe a methodology for the synthesis of extended aromatic structures through dehydrative C-C coupling from easily accessible diols. Treatment of the diols with a Brønsted acid induces nucleophilic addition of an arene or heteroarene, yielding fully aromatic products in up to 99% yield with thiophenes, furan, indole, and <i>N</i>,<i>N</i>-dimethylaniline as coupling partners. The C-C coupling reaction proceeds under mild conditions and offers high atom economy. The development of this methodology and its application to the synthesis of unsymmetrically substituted molecules and cycloaromatization reactions will be discussed.

Extended π-conjugated structures through dehydrative arene-arene coupling

256th National Meeting (2018)

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