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Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur

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† Integrated Research Consortium on Chemical Sciences, Nagoya University, Chikusa, Nagoya 464-8602, Japan
‡ Graduate School of Science, Nagoya University, Chikusa, Nagoya, Japan
§ JST, ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya, Japan
∥ Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, Japan
*[email protected] (Y.S.)
*[email protected] (K.I.)
Cite this: J. Am. Chem. Soc. 2016, 138, 32, 10351–10355
Publication Date (Web):August 8, 2016
https://doi.org/10.1021/jacs.6b06486
Copyright © 2016 American Chemical Society
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    Abstract

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    A simple yet effective method for the formation of thiophene-fused π-systems is reported. When arylethynyl-substituted polycyclic arenes were heated in DMF in the presence of elemental sulfur, the corresponding thiophene-fused polycyclic arenes were obtained via cleavage of the ortho-C–H bond. Thus, arylethynylated naphthalenes, fluoranthenes, pyrenes, corannulenes, chrysenes, and benzo[c]naphtho[2,1-p]chrysenes were effectively converted into the corresponding thiophene-fused π-systems. Apart from polycyclic hydrocarbons, thiophene derivatives are also susceptible to this reaction. The practical utility of this reaction is demonstrated by preparations on the decagram scale, one-pot two-step reaction sequences, and multiple thiophene annulations.

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