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Fe-Catalyzed Nucleophilic Activation of C–Si versus Allylic C–O Bonds: Catalytic Trifluoromethylation of Carbonyl Groups versus Tandem Trifluormethylation–Allylation of Olefins

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journal contribution
posted on 27.10.2014, 00:00 by Johannes E. M. N. Klein, Susanne Rommel, Bernd Plietker
The nucleophilic ferrate salt Bu4N­[Fe­(CO)3(NO)] (TBA­[Fe]) is able to catalyze the direct trifluoromethylation of aldehydes and ketones using Me3SiCF3 as a trifluoromethylating agent. Interception of the C–Si σ-bond activation using allylic acetates allows for a tandem trifluoromethylation–allylation of electron-deficient olefins. The higher activity of acetate in the C–Si bond activation and the selective Fe-catalyzed activation of the allylic acetate are prerequisites for this unprecedented three-component coupling reaction.