TY - JOUR
T1 - N-Heterocycle-Fused Pentalenes by a Gold-Catalyzed Annulation of Diethynyl-Quinoxalines and -Phenazines
AU - Sekine, Kohei
AU - Stuck, Fabian
AU - Schulmeister, Jürgen
AU - Wurm, Thomas
AU - Zetschok, Dominik
AU - Rominger, Frank
AU - Rudolph, Matthias
AU - Hashmi, A. Stephen K.
N1 - Funding Information:
The authors are grateful to funding by the DFG (SFB 1249-NHeteropolyzyklen als Funktionsmaterialien).
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/8/27
Y1 - 2018/8/27
N2 - 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.
AB - 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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U2 - 10.1002/chem.201803096
DO - 10.1002/chem.201803096
M3 - Article
C2 - 29923240
AN - SCOPUS:85050341737
SN - 0947-6539
VL - 24
SP - 12515
EP - 12518
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 48
ER -