Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur
Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur
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DOI：
10.1021/jacs.6b06486
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发表时间：
2016-08-17
影响因子：
15
通讯作者：
Itami, Kenichiro
中科院分区：
文献类型：
--
作者：
Meng, Lingkui;Fujikawa, Takao;Itami, Kenichiro
本文报道了一种简单而有效的噻吩稠合π-体系的合成方法。芳基乙炔基取代的多环芳烃在DMF中加热时，通过邻位CH键的断裂得到相应的噻吩稠合多环芳烃。因此，芳基乙炔化的萘，荧蒽，芘，corannulene，屈，和苯并[c]萘并[2，1-p]屈有效地转化为相应的噻吩稠合π-系统。除了多环烃之外，噻吩衍生物也对该反应敏感。该反应的实际效用是通过十克规模的制备，一锅两步反应序列，和多个噻吩成环。
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.