Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 32, Pages 10351-10355Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b06486
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Funding
- ERATO program from JST
- MEXT [16K05771]
- Integrated Research Consortium on Chemical Sciences
- World Premier International Research Center (WPI) Initiative, Japan
- Grants-in-Aid for Scientific Research [14J10460, 16K05771] Funding Source: KAKEN
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A simple yet effective method for the formation of thiophene-fused pi-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-CH bond. Thus, arylethynylated naphthalenes, fluoranthenes, pyrenes, corannulenes, chrysenes, and benzo[c]naphtho-[2,1-p]chrysenes were effectively converted into the corresponding thiophene-fused pi-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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