Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 4, Pages 1067-1071Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201307846
Keywords
fluorine; heterocycles; hypervalent iodine; radicals; synthetic methods
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Funding
- Nanyang Technological University
- Singapore Ministry of Education (Academic Research Fund) [MOE2012-T2-1-014]
- Lee Kuan Yew postdoctoral fellowship
- Ecole Polytechnique
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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.
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