Unexpected Reactivity of Trifluoromethyl Diazomethane (CF3CHN2): Electrophilicity of the Terminal N-Atom

被引:61
作者
Arkhipov, Anton V. [1 ,2 ]
Arkhipov, Viatcheslav V. [1 ,2 ]
Cossy, Janine [3 ]
Kovtunenko, Volodymir O. [2 ]
Mykhailiuk, Pavel K. [1 ,2 ,3 ]
机构
[1] Enamine Ltd, Chervonotkatska 78, UA-02094 Kiev, Ukraine
[2] Natl Taras Shevchenko Univ Kyiv, Dept Chem, Volodymyrska 64, UA-01033 Kiev, Ukraine
[3] PSL Res Univ, UMR 8231, Inst Chem Biol & Innovat CBI, Lab Chim Organ,ESPCI ParisTech,CNRS, 10 Rue Vauquelin, F-75231 Paris 05, France
关键词
IN-SITU GENERATION; ELECTRON-DEFICIENT ALKYNES; ION CATALYZED HOMOLOGATION; AMINO-ACID ESTERS; MEDICINAL CHEMISTRY; PERFLUOROALKYLATION REACTIONS; DIASTEREOSELECTIVE SYNTHESIS; FLUORINATED PYRAZOLES; 3-COMPONENT SYNTHESIS; ALKYLBORON COMPOUNDS;
D O I
10.1021/acs.orglett.6b01565
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
After more than 70 years since its discovery, CF3CHN2 was found to possess a novel reactivity mode: N-terminal electrophile. With C-nucleophiles it gives hydrazones that are easily transformed into valuable CF3-heterocycles.
引用
收藏
页码:3406 / 3409
页数:4
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