Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
Angew Chem Int Ed Engl. 2014 Jan 20;53(4):1067-71. doi: 10.1002/anie.201307846. Epub 2013 Dec 11.
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 Me3 SiCF3 to efficiently generate α-trifluoromethyl azines. The resulting α-trifluoromethyl azines were successfully transformed to valuable fluorine-containing molecules such as α-trifluoromethyl ketones, β-trifluoromethyl amines, 5-fluoropyrazoles, and trifluoroethyl isoquinolines.
含氟有机基团由于其独特的性质,如吸电子性、代谢稳定性和亲脂性,在药物、农用化学品和功能材料中变得越来越重要。本文描述了 PhI(OAc)2 介导的乙烯基叠氮与 Me3SiCF3 的自由基三氟甲基化反应,有效地生成了α-三氟甲基氮杂环丙烷。所得的α-三氟甲基氮杂环丙烷可以成功转化为有价值的含氟分子,如α-三氟甲基酮、β-三氟甲基胺、5-氟吡唑和三氟乙基异喹啉。