环加成
化学
化学选择性
分子内力
炔烃
组合化学
胺气处理
催化作用
分子间力
立体化学
有机化学
分子
作者
Yujuan Xie,Liliang Huang,Huihui Feng,Yayu Qi,Erik V. Van der Eycken,Huangdi Feng
出处
期刊:Organic Letters
[American Chemical Society]
日期:2022-08-25
卷期号:24 (34): 6346-6350
被引量:6
标识
DOI:10.1021/acs.orglett.2c02606
摘要
Disclosed herein is an efficient strategy for the synthesis of 2,4,5-trisubstituted pyridines via CuI/NBS-catalyzed formal intermolecular [2+2+2] cycloaddition of easily available primary amines and nonactivated terminal alkynes. Moreover, this given reaction features a new mode of cycloaddition with high regio- and chemoselectivity, good atom- and step-economy, broad substrate scope, and wide functional group compatibility. Further mechanism studies indicate that this transformation starts with oxidative alkynylation of the amine to form a propargylamine intermediate, followed by radical addition to the alkyne and intramolecular cycloaddition, delivering the pharmacologically interesting multisubstituted pyridines.
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