Fe-catalyzed nucleophilic activation of c-si versus allylic C-O bonds: Catalytic trifluoromethylation of carbonyl groups versus tandem trifluormethylation-allylation of olefins

Johannes E.M.N. Klein, Susanne Rommel, Bernd Plietker

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

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 I-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.

Original languageEnglish (US)
Pages (from-to)5802-5810
Number of pages9
JournalOrganometallics
Volume33
Issue number20
DOIs
StatePublished - Oct 27 2014

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