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PhI(OAc)(2) 介导的乙烯基叠氮化物与 Me(3)SiCF(3)的三氟甲基化反应。

PhI(OAc)(2) -mediated radical trifluoromethylation of vinyl azides with Me(3)SiCF(3).

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).

出版信息

Angew Chem Int Ed Engl. 2014 Jan 20;53(4):1067-71. doi: 10.1002/anie.201307846. Epub 2013 Dec 11.

Abstract

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.

摘要

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。

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