Palladium-Catalyzed Tandem Cyclization Strategy for the Assembly of 3-Halo-1,2,5-triarylpyrroles from N-Alkylanilines and Haloalkynes

被引:8
|
作者
Fang, Songjia [1 ]
Jiang, Huanfeng [1 ]
Wu, Wanqing [1 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China
来源
CHINESE JOURNAL OF CHEMISTRY | 2023年 / 41卷 / 02期
基金
中国国家自然科学基金;
关键词
Palladium-catalyzed; Haloalkynes; N-Alkylanilines; Cyclization; Halopyrroles; Amines; Insertion; Synthetic methods; INTERMOLECULAR OXIDATIVE CYCLIZATION; C-H ALKYNYLATION; PYRROLE; BROMOALKYNES; ANNULATION; ALKALOIDS; SCOPE;
D O I
10.1002/cjoc.202200422
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This report discloses a distinctive palladium-catalyzed sequential tandem cyclization reaction of two molecular haloalkynes and one molecular N-alkylanilines, leading to the efficient assembly of various 3-halo-1,2,5-triarylpyrrole derivatives. Two carbon-carbon triple bonds and one carbon-halogen bond in two molecular haloalkynes are transformed conveniently in one single step, which may involve the aminoalkynylation of haloalkyne and cyclization of the newly formed enyne intermediate. The high chemo-and regioselectivities, good functional group tolerance and late-stage modification of the halopyrrole products further illustrate the synthetic value of this strategy.
引用
收藏
页码:181 / 187
页数:7
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