N-Heterocycle-fused Pentalenes by a Gold-catalyzed annulation of Diethynyl-Quinoxalines and -Phenazines
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 inc...
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| Main Authors: | , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
August 27, 2018
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| In: |
Chemistry - a European journal
Year: 2018, Volume: 24, Issue: 48, Pages: 12515-12518 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201803096 |
| Online Access: | Resolving-System, Volltext: http://dx.doi.org/10.1002/chem.201803096 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201803096 
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| Author Notes: | Kohei Sekine, Fabian Stuck, Jürgen Schulmeister, Thomas Wurm, Dominik Zetschok, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi |
| Summary: | 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. |
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| Item Description: | Gesehen am 11.12.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201803096 |