N-Heterocycle-Fused Pentalenes by a Gold-Catalyzed Annulation of Diethynyl-Quinoxalines and -Phenazines

Kohei Sekine, Fabian Stuck, Jürgen Schulmeister, Thomas Wurm, Dominik Zetschok, Frank Rominger, Matthias Rudolph, A. Stephen K. Hashmi

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8 Citations (Scopus)

Abstract

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 °C, which usually leads to catalyst decomposition in gold catalysis. At 130 °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.

Original languageEnglish
Pages (from-to)12515-12518
Number of pages4
JournalChemistry - A European Journal
Volume24
Issue number48
DOIs
Publication statusPublished - Aug 27 2018
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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    Sekine, K., Stuck, F., Schulmeister, J., Wurm, T., Zetschok, D., Rominger, F., Rudolph, M., & Hashmi, A. S. K. (2018). N-Heterocycle-Fused Pentalenes by a Gold-Catalyzed Annulation of Diethynyl-Quinoxalines and -Phenazines. Chemistry - A European Journal, 24(48), 12515-12518. https://doi.org/10.1002/chem.201803096