Copper-Mediated Trifluoromethylation of α-Diazo Esters with TMSCF3: The Important Role of Water as a Promoter

被引：157

作者：

Hu, Mingyou ^{[1
]}

Ni, Chuanfa ^{[1
]}

Hu, Jinbo ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 37期

基金：

中国国家自然科学基金;

关键词：

MEDICINAL CHEMISTRY; DOUBLE INSERTION; FLUORINE; BOND; (TRIFLUOROMETHYL)COPPER; DIFLUOROMETHYLENE; CATALYSIS; EFFICIENT; COMPLEX;

D O I：

10.1021/ja307058c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper-mediated trifluoromethylation of alpha-diazo esters with TMSCF3 reagent has been developed as a new method to prepare alpha-trifluoromethyl esters. This trifluoromethylation reaction represents the first example of fluoroalkylation of a non-fluorinated carbene precursor. Water plays an important role in promoting the reaction by activating the "CuCF3" species prepared from Cull TMSCF3/CsF (1.0:1.1:1.1). The scope of this trifluoromethylation reaction is broad, and its efficiency is demonstrated in the synthesis of a variety of aryl-, benzyl-, and alkyl-substituted 3,3,3-trifluoropropanoates.

引用

页码：15257 / 15260

页数：4

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