title: Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur.
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.
authors: Integrated Research Consortium on Chemical Sciences, Nagoya University , Chikusa, Nagoya 464-8602, Japan.|Graduate School of Science, Nagoya University , Chikusa, Nagoya, Japan.
authors: Lingkui
authors: L
authors: Meng
authors: Graduate School of Science, Nagoya University , Chikusa, Nagoya, Japan.
authors: Takao
authors: T
authors: Fujikawa
authors: Graduate School of Science, Nagoya University , Chikusa, Nagoya, Japan.|JST, ERATO, Itami Molecular Nanocarbon Project, Nagoya University , Chikusa, Nagoya, Japan.
authors: Motonobu
authors: M
authors: Kuwayama
authors: Graduate School of Science, Nagoya University , Chikusa, Nagoya, Japan.|JST, ERATO, Itami Molecular Nanocarbon Project, Nagoya University , Chikusa, Nagoya, Japan.
authors: Yasutomo
authors: Y
authors: Segawa
authors: 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.
authors: Kenichiro
authors: K
authors: Itami