Display options
Cite
Meng L, Fujikawa T, Kuwayama M, et al. Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur. J Am Chem Soc. 2016;138(32):10351-5doi: 10.1021/jacs.6b06486.
Meng, L., Fujikawa, T., Kuwayama, M., Segawa, Y., & Itami, K. (2016). Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur. Journal of the American Chemical Society, 138(32), 10351-5. https://doi.org/10.1021/jacs.6b06486
Meng, Lingkui, et al. "Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur." Journal of the American Chemical Society vol. 138,32 (2016): 10351-5. doi: https://doi.org/10.1021/jacs.6b06486
Meng L, Fujikawa T, Kuwayama M, Segawa Y, Itami K. Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur. J Am Chem Soc. 2016 Aug 17;138(32):10351-5. doi: 10.1021/jacs.6b06486. Epub 2016 Aug 08. PMID: 27501373.
Copy Download .nbib Format: NLM
Share it on

J Am Chem Soc. 2016 Aug 17;138(32):10351-5. doi: 10.1021/jacs.6b06486. Epub 2016 Aug 08.

Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur.

Journal of the American Chemical Society

Lingkui Meng, Takao Fujikawa, Motonobu Kuwayama, Yasutomo Segawa, Kenichiro Itami

Affiliations

  1. Integrated Research Consortium on Chemical Sciences, Nagoya University , Chikusa, Nagoya 464-8602, Japan.
  2. Graduate School of Science, Nagoya University , Chikusa, Nagoya, Japan.
  3. JST, ERATO, Itami Molecular Nanocarbon Project, Nagoya University , Chikusa, Nagoya, Japan.
  4. Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University , Chikusa, Nagoya, Japan.

PMID: 27501373 DOI: 10.1021/jacs.6b06486

Abstract

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.

Publication Types