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

被引：10

作者：

Li, Sen ^{[1
]}

Jie, Kun ^{[1
]}

Yan, Wenjie ^{[1
]}

Pan, Qingjun ^{[1
]}

Zhang, Min ^{[1
]}

Wang, Yufeng ^{[1
]}

Fu, Zhengjiang ^{[1
]}

Guo, Shengmei ^{[1
]}

Cai, Hu ^{[1
]}

机构：

[1] Nanchang Univ, Dept Chem, 999 Xuefu Rd, Nanchang 330031, Jiangxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 89期

基金：

中国国家自然科学基金;

关键词：

CARBON-CARBON BOND; DECARBONYLATIVE BORYLATION; DIRECT AMINATION; GENERAL-METHOD; KETONES; ACYL; SECONDARY; TRANSAMIDATION; ACTIVATION; FUNCTIONALIZATION;

D O I：

10.1039/d0cc04960c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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/O-2 shows the best catalytic result at 150 degrees 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.

引用

页码：13820 / 13823

页数：4

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