重氮
化学
功能群
分子
组合化学
有机化学
聚合物
作者
Qichun Zhang,Yanchuan Li,Shao‐Fei Ni,Jinpeng Li,Dengmei Xia,Xinyu Han,Jiu‐Dong Lin,Jinxin Wang,Shoubhik Das,Wensheng Zhang
出处
期刊:Chemical Science
[The Royal Society of Chemistry]
日期:2023-01-01
卷期号:14 (38): 10411-10419
摘要
To date, [3 + 2] cycloadditions of diazo esters with alkynes or alkenes have been a robust tool to generate pyrazoles and pyrazolines. However, methods capable of generating donor/donor diazo species from readily available N-tosylhydrazones to furnish [3 + 2] cycloadditions, remain elusive. Herein, we describe the first visible-light-induced [3 + 2] cycloadditions of donor/donor diazo precursors with alkenes to afford pyrazoles and novel (spiro)pyrazolines bearing a quaternary center. This protocol shows a tolerable substrate scope covering versatile carbonyl compounds and alkenes. Late-stage functionalization of bioactive molecules, one-pot approach, and gram-scale synthesis have also been introduced successfully to prove the practicability. At last, mechanistic experiments and DFT studies suggested the formation of non-covalent interactions enabling the activation of N-tosylhydrazones and the formation of the donor/donor diazo intermediates.
科研通智能强力驱动
Strongly Powered by AbleSci AI