化学
合成子
戒指(化学)
环加成
区域选择性
组合化学
双金属片
催化作用
有机合成
立体化学
有机化学
作者
Ruirui Li,Bo Li,Hongpeng Zhang,Cheng‐Wei Ju,Ying Qin,Xiao‐Song Xue,Dongbing Zhao
出处
期刊:Nature Chemistry
[Springer Nature]
日期:2021-07-19
卷期号:13 (10): 1006-1016
被引量:59
标识
DOI:10.1038/s41557-021-00746-7
摘要
The development of innovative strategies for the synthesis of N-heterocyclic compounds is an important topic in organic synthesis. Ring expansion methods to form large N-heterocycles often involve the cycloaddition of strained aza rings with π bonds. However, in some cases such strategies suffer from some limitations owing to the difficulties in controlling the regioselectivity and the accessibility of specific π-bond synthons. Here, we report the development of a general ring expansion strategy that involves a formal cross-dimerization between three-membered aza heterocycles and three- and four-membered-ring ketones through synergistic bimetallic catalysis. These formal cross-dimerizations of two different strained rings are efficient and scalable, and provide a straightforward and broadly applicable means of assembling diverse N-heterocycles, such as 3-benzazepinones, dihydropyridinones and uracils, which are versatile units in numerous drugs and biologically active compounds. Preliminary mechanistic studies revealed that the C–C bond of strained ring ketones is first cleaved by the Pd0 species during the reaction. Using synergistic bimetallic catalysis, a general ring expansion strategy has been developed for cross-dimerization between three-membered aza heterocycles and three- and four-membered-ring ketones. This method provides a straightforward and broadly applicable route for the assembly of 3-benzazepinones, dihydropyridinones and uracils, which are versatile units in numerous drugs and biologically active compounds.
科研通智能强力驱动
Strongly Powered by AbleSci AI