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：85
|
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
收藏
页码：6004 / 6007
页数：4
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