Scope and regioselectivity of the 1,3-dipolar cycloaddition of azides with methyl 2-perfluoroalkynoates for an easy, metal-free route to perfluoroalkylated 1,2,3-triazoles

被引：33

作者：

Wei, Jiamei ^{[1
]}

Chen, Jie ^{[1
]}

Xu, Jiechao ^{[1
]}

Cao, Long ^{[1
]}

Deng, Hongmei ^{[4
]}

Sheng, Weihua ^{[5
]}

Zhang, Hui ^{[1
]}

Cao, Weiguo ^{[1
,2
,3
]}

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[3] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[4] Shanghai Univ, Lab Microstruct, Shanghai 200444, Peoples R China

[5] Shanghai Inst Space Prop, Shanghai 200233, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2012年 / 133卷

基金：

中国国家自然科学基金;

关键词：

Methyl; 2-perfluoroalkynoates; 1,2,3-Triazoles; 1,3-Dipolar cycloaddition; Metal-free; CLICK CHEMISTRY; ORGANIC AZIDES; ALKYNES; FACILE;

D O I：

10.1016/j.jfluchem.2011.09.009

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions of methyl 2-perfluoroalkynoates with various azides have been examined, leading to a simple metal-free synthetic protocol for the synthesis of perfluoroalkylated 1,2,3-triazoles. The regiochemical results demonstrated that the cycloaddition was controlled by FMO (the frontier molecular obitals) interaction and steric hindrance in transition states. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：146 / 154

页数：9

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