Copper(I)-Catalyzed Dehydrogenative Amidation of Arenes Using Air as the Oxidant

The copper(I) bromide‐catalyzed intermolecular dehydrogenative amidation of arenes via CH bond activation assisted by a 2‐pyridyl or 1‐pyrazolyl chelating group using air as the terminal oxidant has been achieved at 140 °C. N‐Aryl amides, N‐alkyl amides, benzamide derivatives, imides, and lactams a...

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Veröffentlicht in:Advanced synthesis & catalysis 2015-04, Vol.357 (6), p.1311-1315
Hauptverfasser: Li, Gang, Jia, Chunqi, Chen, Qingliang, Sun, Kai, Zhao, Feng, Wu, Hankui, Wang, Zhiyong, Lv, Yunhe, Chen, Xiaolan
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Sprache:eng
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Zusammenfassung:The copper(I) bromide‐catalyzed intermolecular dehydrogenative amidation of arenes via CH bond activation assisted by a 2‐pyridyl or 1‐pyrazolyl chelating group using air as the terminal oxidant has been achieved at 140 °C. N‐Aryl amides, N‐alkyl amides, benzamide derivatives, imides, and lactams all are good coupling partners to obtain moderate to excellent yields. The amount of solvent is critical for the transformation: both increasing and decreasing the amount of solvent decreased the yield. Notably, the amidation of bimolecular 2‐phenylpyridine with the dual NH bonds of a primary amide proceeded smoothly in one‐pot to afford a good yield under the same conditions. The amidation can be performed with a good yield at the gram scale.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400883