Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds

被引：53

作者：

Chen, Gui ^{[1
]}

Song, Jinshuai ^{[2
]}

Yu, Yinghua ^{[1
]}

Luo, Xuesong ^{[1
]}

Li, Chunsen ^{[2
]}

Huang, Xueliang ^{[1
]}

机构：

[1] Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Yangqiao West Rd 155, Fuzhou 350002, Fujian, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Yangqiao West Rd 155, Fuzhou 350002, Fujian, Peoples R China

来源：

CHEMICAL SCIENCE | 2016年 / 7卷 / 03期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM-CATALYZED INSERTION; HIGHLY ENANTIOSELECTIVE INSERTION; C-C BOND; DIAZO-COMPOUNDS; CARBENE INSERTION; H INSERTION; ASYMMETRIC FLUORINATION; ALPHA-DIAZOESTERS; ORGANIC-SYNTHESIS; ACCESS;

D O I：

10.1039/c5sc04237b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Gem-aminofluorination of diazocarbonyl compounds has been achieved for the first time. This reaction proceeds under mild conditions and does not require any transition-metal promoter or catalyst. Treatment of diazoesters with N-fluorobenzenesulfonimide (NFSI), which serves as both a fluorine and nitrogen source, results in the facile construction of C-N and C-F bonds, providing aminofluorination products in moderate to excellent yields. Kinetic studies and DFT calculations have provided valuable insight into the potential mechanism for this novel N-F bond insertion.

引用

页码：1786 / 1790

页数：5

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