PhI(OAc)2 mediated radical trifluoromethylation of vinyl azides with Me3SiCF3

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 trifluoromethyla...

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Bibliographic Details
Main Authors: Wang, Yi-Feng, Lonca, Geoffroy Hervé, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
Online Access:https://hdl.handle.net/10356/103036
http://hdl.handle.net/10220/19137
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Institution: Nanyang Technological University
Language: English
Description
Summary: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 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.