Diversity-Oriented Approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-Substituted Arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes

被引：83

作者：

Emer, Enrico ^{[1
]}

Twilton, Jack ^{[1
]}

Tredwell, Matthew ^{[1
]}

Calderwood, Samuel ^{[1
]}

Collier, Thomas Lee ^{[3
]}

Liegault, Benoit ^{[1
,2
]}

Taillefer, Marc ^{[2
]}

Gouvemeur, Veronique ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

[2] ENSCM, Inst Charles Gerhardt Montpellier, CNRS, UMR 5253,AM2N, F-34296 Montpellier 5, France

[3] Advion BioSyst, Ithaca, NY 14850 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 22期

基金：

英国工程与自然科学研究理事会;

关键词：

ALPHA-DIAZO ESTERS; PENTAFLUOROETHYL COPPER; ACID-DERIVATIVES; TRIFLUOROMETHYLATION; FLUORINE; ARYL; PERFLUOROALKYLATION; HYDROFLUORINATION; PHARMACEUTICALS; BROMIDES;

D O I：

10.1021/ol5030184

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arenes substituted with perfluoroalkyl groups are attractive targets for drug and agrochemical development. Exploiting the carbenic character of donor/acceptor diazo compounds, a diversity-oriented synthesis of perfluoroalkylated arenes, for late stage fluorofunctionalization, is described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)arenes with HF, F/Br, F-2, CF3H, and CF3SH sources give direct access to a variety of perfluoroalkyl-substituted arenes presenting with incremental fluorine content. The value of this approach is also demonstrated for radiochemistry and positron emission tomography with the [F-18]-labeling of CF3CHF-, CF3CBrF-, and CF3CF2-arenes from [F-18]fluoride.

引用

页码：6004 / 6007

页数：4

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