Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones

被引：12

作者：

Vaclavik, Jiri ^{[1
,2
]}

Chernykh, Yana ^{[1
]}

Jurasek, Bronislav ^{[1
,2
]}

Beier, Petr ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague, Czech Republic

[2] Inst Chem Technol, Dept Organ Chem, CR-16628 Prague, Czech Republic

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2015年 / 169卷

关键词：

Fluorine; Tetrafluoroethylation; Sulfones; Nucleophilic addition; Carbonyl compounds; TRIFLUOROMETHYLATION; FLUOROALKYLATION; EXCHANGE; ALKENES; ALKYNES;

D O I：

10.1016/j.jfluchem.2014.10.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Global interest in the "CF2CF2" building blocks (tetrafluoroethylene, tetrafluoroethyl) is still rather marginal. One of the main reasons is the lack of efficient and selective tetrafluoroethylation reagents. In this context, we present here three new reagents (PhSO2CF2CF2R, R = SiMe3, SiEt3 and H) capable of nucleophilic addition to carbonyl compounds, thus affording rare alcohols containing the CF2CF2 motif. The experimental observations are complemented with a brief computational study which confirmed that the reactivity of the nudeophilic reagents is strongly dependent on electronic properties of substituents on both ends of the CF2CF2 group. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：24 / 31

页数：8

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