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Issue 12, 2017
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Transition metal-free stereospecific access to (E)-(1-fluoro-2-arylvinyl)phosphine borane complexes

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Abstract

This work describes the first transition metal-free stereospecific synthesis of (E)-(1-fluoro-2-arylvinyl)phosphine boranes through the addition of diarylphosphine-boranes to gem-bromofluoroalkenes in the presence of a base at room temperature. The reaction proceeds well under very mild conditions and tolerates a variety of functionalities. Scope and limitations of the reaction are discussed. Mechanistic investigations have been undertaken and revealed that the reaction takes place through an SRN1 mechanism. The formation of the fluorinated vinyl radical has been evidenced by electron paramagnetic resonance (EPR) experiment.

Graphical abstract: Transition metal-free stereospecific access to (E)-(1-fluoro-2-arylvinyl)phosphine borane complexes

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Publication details

The article was received on 06 Dec 2016, accepted on 21 Jan 2017 and first published on 23 Jan 2017


Article type: Communication
DOI: 10.1039/C6CC09673E
Citation: Chem. Commun., 2017,53, 2048-2051
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    Transition metal-free stereospecific access to (E)-(1-fluoro-2-arylvinyl)phosphine borane complexes

    K. Rousée, X. Pannecoucke, A. Gaumont, J. Lohier, F. Morlet-Savary, J. Lalevée, J. Bouillon, S. Couve-Bonnaire and S. Lakhdar, Chem. Commun., 2017, 53, 2048
    DOI: 10.1039/C6CC09673E

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