Photoredox-Catalyzed Alkynylation of C(sp3)-H Bonds Adjacent to a Nitrogen Atom of Tertiary Amines with Alkynyl Bromides

被引：3

作者：

Dai, Jin-Long ^{[1
,2
]}

Wang, Tao ^{[1
,2
]}

Hao, Yan ^{[1
,2
]}

Zhang, Yue ^{[1
,2
]}

Yan, Shenghu ^{[1
,2
]}

Li, Guigen ^{[3
]}

Wang, Jia-Yin ^{[1
,2
]}

机构：

[1] Changzhou Univ, Sch Pharm, Changzhou 213164, Jiangsu, Peoples R China

[2] Changzhou Univ, Continuous Flow Engn Lab Natl Petr & Chem Ind, Changzhou 213164, Jiangsu, Peoples R China

[3] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 21期

关键词：

FUNCTIONALIZATION; PROPARGYLAMINE; ANNULATION; IMINES;

D O I：

10.1021/acs.joc.4c02065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and robust alkynylation of C(sp(3))-H bonds adjacent to a nitrogen atom of tertiary amines with alkynyl bromides as radical alkynylating reagents has been realized under visible-light irradiation. A range variety of tertiary amines including N-arylamines and N-alkylamine have been coupled with both aromatic and aliphatic alkynyl bromides to furnish 51 examples of propargylamines in moderate to excellent yields (31-80% yields). The possible mechanism was a radical addition-elimination process based on preliminary mechanistic studies.

引用

页码：15901 / 15913

页数：13

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