Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation and Beyond

被引：995

作者：

Liu, Xiao ^{[1
]}

Xu, Cong ^{[1
]}

Wang, Mang ^{[1
]}

Liu, Qun ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

来源：

CHEMICAL REVIEWS | 2015年 / 115卷 / 02期

关键词：

COPPER-CATALYZED TRIFLUOROMETHYLATION; RUPPERT-PRAKASH REAGENT; SILVER-MEDIATED TRIFLUOROMETHYLATION; AMINO-ALPHA-TRIFLUOROMETHYL; HYPERVALENT IODINE REAGENT; N-HETEROCYCLIC CARBENES; ENANTIOSELECTIVE ALLYLIC TRIFLUOROMETHYLATION; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; DECARBOXYLATIVE ALDOL REACTION; QUATERNARY AMMONIUM FLUORIDES;

D O I：

10.1021/cr400473a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of C-CF3 bond forming reactions have been developed from various trifluoromethylating reagents, in the 30 years since trifluoromethyltrimethylsilane (TMSCF3) was synthesized from CF3Br (an ozone depleting compound) and trimethylsilyl chloride in 1984, TMSCF3 (Ruppert-Prakash reagent) has been and is still the most important CF3-centered nucleophilic trifluoromethylating reagent. Ruppert-Prakash reagent is now also a useful starting material for the synthesis of potassium (trifluoromethyl)- trimethoxyborate, the well-defined trifluoromethyl copper compounds, trifluoromethanesulfanylamides/trifluoromethanesulfanamides used in trifluoromethylthiolation, difluoromethyltriflate as a convenient source of difluorocarbene, (difluoromethyl)trimethylsilane (TMSCF2H) used in difluoromethylation reactions, Togni's reagents and related species as electrophilic trifluoromethylating reagents.

引用

页码：683 / 730

页数：48

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