PhI(OAc)2-Mediated Radical Trifluoromethylation of Vinyl Azides with Me3SiCF3

被引:144
作者
Wang, Yi-Feng [1 ]
Lonca, Geoffroy Herve [1 ]
Chiba, Shunsuke [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
fluorine; heterocycles; hypervalent iodine; radicals; synthetic methods; COPPER-CATALYZED TRIFLUOROMETHYLATION; ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; SILVER-MEDIATED TRIFLUOROMETHYLATION; C-H TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; OXIDATIVE TRIFLUOROMETHYLATION; SANDMEYER TRIFLUOROMETHYLATION; 1,3-DICARBONYL COMPOUNDS; UNACTIVATED OLEFINS; SUBSTITUTED KETONES;
D O I
10.1002/anie.201307846
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The fluorine-containing organic motif is becoming privileged in pharmaceuticals, agrochemicals, and functional materials, owing to its unique properties such as electron-withdrawing character, metabolic stability, and lipophilicity. Described herein is the PhI(OAc)(2)-mediated radical trifluoromethylation of vinyl azides with Me3SiCF3 to efficiently generate -trifluoromethyl azines. The resulting -trifluoromethyl azines were successfully transformed to valuable fluorine-containing molecules such as -trifluoromethyl ketones, -trifluoromethyl amines, 5-fluoropyrazoles, and trifluoroethyl isoquinolines.
引用
收藏
页码:1067 / 1071
页数:5
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