Copper-Catalyzed Carbonylative Coupling of Cycloalkanes and Amides

Carbonylation reactions are a most powerful method for the synthesis of carbonyl‐containing compounds. However, most known carbonylation procedures still require noble‐metal catalysts and the use of activated compounds and good nucleophiles as substrates. Herein, we developed a copper‐catalyzed carb...

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Veröffentlicht in:Angewandte Chemie International Edition 2016-06, Vol.55 (25), p.7227-7230
Hauptverfasser: Li, Yahui, Dong, Kaiwu, Zhu, Fengxiang, Wang, Zechao, Wu, Xiao-Feng
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Sprache:eng
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Zusammenfassung:Carbonylation reactions are a most powerful method for the synthesis of carbonyl‐containing compounds. However, most known carbonylation procedures still require noble‐metal catalysts and the use of activated compounds and good nucleophiles as substrates. Herein, we developed a copper‐catalyzed carbonylative transformation of cycloalkanes and amides. Imides were prepared in good yields by carbonylation of a C(sp3)−H bond of the cycloalkane with the amides acting as weak nucleophiles. Notably, this is the first report of copper‐catalyzed carbonylative C−H activation. A copper‐catalyzed carbonylative synthesis of imides starting from cycloalkanes and amides has been developed. The imides were prepared in good yields by carbonylation of a C(sp3)−H bond of the cycloalkane with the amides acting as weak nucleophiles (DTBP=di‐tert‐butylperoxide, 1,10‐phen=1,2‐phenanthroline hydrate).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201603235