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Copper‐Mediated C6‐Selective Dehydrogenative Heteroarylation of 2‐Pyridones with 1,3‐Azoles
Author(s) -
Odani Riko,
Hirano Koji,
Satoh Tetsuya,
Miura Masahiro
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406228
Subject(s) - substituent , chemistry , catalysis , copper , selectivity , ring (chemistry) , salt (chemistry) , medicinal chemistry , nitrogen atom , combinatorial chemistry , organic chemistry
A copper‐mediated C6‐selective dehydrogenative heteroarylation of 2‐pyridones with 1,3‐azoles has been developed. The reaction proceeded smoothly by twofold CH cleavage even in the absence of noble‐metal catalysts. The observed site selectivity was directed by a pyridyl substituent on the nitrogen atom of the pyridone ring. This directing group was readily removed after the coupling event, thus leading to 2‐pyridone derivatives with a free NH group. Moreover, in some cases, catalytic turnover of the Cu salt was also possible with the ideal terminal oxidant: molecular oxygen in air.