Synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane

被引：33

作者：

Han, Hang ^{[1
]}

Zhu, Bingbin ^{[2
]}

Du, Xiaofan ^{[1
]}

Zhu, Yu ^{[1
]}

Yu, Chuanming ^{[1
]}

Jiang, Xinpeng ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou, Peoples R China

[2] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou, Peoples R China

来源：

GREEN CHEMISTRY | 2021年 / 23卷 / 24期

基金：

中国国家自然科学基金;

关键词：

CLICK CHEMISTRY; ORGANIC AZIDES; METAL; ALKENES; INDOLES; REAGENT; DESIGN;

D O I：

10.1039/d1gc03126k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report a novel reaction for the synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane. In this strategy, the azido radical generated from the interaction of PIDA and TMSN3 selectively followed addition to [1.1.1]propellane to form the carbon-centered radical intermediate, which then reacted with a heterocycle to produce the azide-containing 1,3-disubstituted bicyclo[1.1.1]pentane species. This strategy allowed for the direct installation of an azido group, a versatile synthetic handle for the bicyclo[1.1.1]pentane framework. The use of mild and metal-free conditions will provide a highly efficient route to construct azide-containing bicyclo[1.1.1]pentane species with various applications in synthetic organic chemistry.

引用

页码：10132 / 10136

页数：5

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