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

27 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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© 2014 American Chemical Society.

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

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.",

author = "Klein, \{Johannes E.M.N.\} and Susanne Rommel and Bernd Plietker",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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T1 - Fe-catalyzed nucleophilic activation of c-si versus allylic C-O bonds

T2 - Catalytic trifluoromethylation of carbonyl groups versus tandem trifluormethylation-allylation of olefins

AU - Klein, Johannes E.M.N.

AU - Rommel, Susanne

AU - Plietker, Bernd

PY - 2014/10/27

Y1 - 2014/10/27

N2 - 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.

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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ER -

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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