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Dr. Kohei Fuchibe, Masaki Takahashi and Prof. Junji Ichikawa Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles Angewandte Chemie International Edition 51

Version of Record online: 19 OCT 2012 | DOI: 10.1002/anie.201206946

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Replacing the fluorine: 3-Fluorinated pyrazoles were regioselectively synthesized by sequential substitution reactions of 2-trifluoromethyl-1-alkenes (see scheme). SN2′-type reactions of 2-trifluoromethyl-1-alkenes with deprotonated tert-butoxylcarbonyl- or arylhydrazines afforded 1,1-difluoro-1-alkenes, which were tosylated and then treated with NaH to give the desired 3-fluoropyrazoles.

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