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

doi:10.1021/om5005012

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	5802-5810
Number of pages	9
Journal	Organometallics
Volume	33
Issue number	20
DOIs	https://doi.org/10.1021/om5005012
State	Published - Oct 27 2014

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

In: Organometallics, Vol. 33, No. 20, 27.10.2014, p. 5802-5810.

Research output: Contribution to journal › Article › peer-review

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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.",

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AB - 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.

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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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