Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes |
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| Authors: | Dr. Zhensheng Zhao Kevin C. Y. Ma Prof. Dr. Claude Y. Legault Prof. Dr. Graham K. Murphy |
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| Affiliation: | 1. Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, ON, N2L3G1 Canada;2. Department of Chemistry, Université de Sherbrooke, Sherbrooke, Québec, J1K2R1, Canada |
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| Abstract: | Reacting hydrazones of arylaldehydes with Togni's CF3-benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal-free. |
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| Keywords: | fluorine hydrazones hypervalent iodine trifluoromethylation Wolff–Kishner |
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