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Selective C–C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant

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Abstract

Herein, copper-catalyzed direct C–C bond cleavage of amides fused to 8-aminoquinoline as a directing group to form urea in the presence of amines and dioxygen is reported. Compared to the previous C–H aminations of amides via C–H activation, this reaction presents a catalyst and oxidant controlled C–C bond cleavage strategy that enables amidation through a radical process. CuBr/Ag2CO3/O2 shows the best catalytic result at 150 °C. A series of aryl and alkyl amides were compatible with this transformation. Notably, this method provided access to cyclohexanone, one of the most important industrial materials. The pathway of this reaction was investigated.

Graphical abstract: Selective C–C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant

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Article information


Submitted
20 Jul 2020
Accepted
11 Oct 2020
First published
13 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Selective C–C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant

S. Li, K. Jie, W. Yan, Q. Pan, M. Zhang, Y. Wang, Z. Fu, S. Guo and H. Cai, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC04960C

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