Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis  

作　　者：Qi-Chao Shan Yan Zhao Yong Wu Hong-Fei Liu Xin-Hua Duan Li-Na Guo 

机构地区：[1]Department of Chemistry,School of Chemistry,Energy Research Center of Energy Storage Materials and Devices,Ministry of Education,Xi’an Jiaotong University,Xi’an 710049,China [2]State Key Laboratory of Applied Organic Chemistry,Lanzhou University,Lanzhou 730000,China

出　　处：《Science China Chemistry》2024年第11期3798-3806,共9页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China (Nos. 22171220);the Fundamental Research Funds of the Central Universities (No. xtr072022003)。

摘　　要：A regioselective C-C bond cleavage/aminocarbonylation cascade is presented. In recent years, tremendous progress has been made in the alkoxyl radical-mediated C-C bond cleavage of unstrained monocarbocycles. In contrast, the deconstruction and functionalization of bicyclic skeletons has been less developed and has mainly focused on the ring expansion process. Inspired by the aromatization-driven C-C bond cleavage, here we demonstrate a ring-opening/aminocarbonylation cascade under copper catalysis, in which the formation of a stable γ-lactam or succinimide skeleton reverses the selectivity of C-C cleavage. Remarkably, the photo and thermal assistance is not required when the succinimide skeleton is formed during the ring opening process. DFT calculations revealed that this unexpected ring-opening process is thermodynamically and kinetically favourable.

关 键 词：C-C bond cleavage controllable regioselectivity AMINOCARBONYLATION bicyclic alkoxy radical 

分 类 号：O621.251[理学—有机化学]