Selective C-C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant.
Selective C-C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant.
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DOI：
10.1039/d0cc04960c
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发表时间：
2020-10
影响因子：
4.9
通讯作者：
Sen Li;K. Jie;Wenjie Yan;Qi Pan;Min Zhang;Yufeng Wang;Zhengjiang Fu;Shengmei Guo;H. Cai
中科院分区：
文献类型：
--
作者：
Sen Li;K. Jie;Wenjie Yan;Qi Pan;Min Zhang;Yufeng Wang;Zhengjiang Fu;Shengmei Guo;H. Cai
本文报道了在胺和分子氧的存在下，铜催化的与8-氨基喹啉稠合的酰胺的直接C-C键断裂作为导向基团以形成脲。与先前通过C-H活化的酰胺的C-H胺化相比，该反应呈现催化剂和氧化剂控制的C-C键断裂策略，其能够通过自由基过程进行酰胺化。CuBr/Ag_2CO_3/O_2在150 °C时催化效果最好。一系列芳基和烷基酰胺与这种转化相容。值得注意的是，这种方法提供了获得环己酮的途径，环己酮是最重要的工业材料之一。研究了该反应的途径。
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.