期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 48, 页码 12515-12518出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803096
关键词
annulation; diynes; gold catalysis; heterocycles; pentalenes
资金
- DFG [SFB 1249]
The gold-catalyzed annulation of diethynyl N-heterocycles for the synthesis of quinoxaline-/phenazine-based pentalenes and the study of their optoelectronic properties are described. The inhibition of the gold catalyst by the nitrogen centers in the substrate and the product could be overcome by increasing the reaction temperature to 130 degrees C, which usually leads to catalyst decomposition in gold catalysis. At 130 degrees C, 6,7-di(arylethynyl)quinoxalines in chlorobenzene give the corresponding pentalenes. The annulation of 2,3-di(arylethynyl)quinoxalines requires an even higher temperature under microwave irradiation. The quinoxaline-based pentalenes showed lower LUMO levels compared to the corresponding naphthalene-based pentalenes.
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