Issue 12, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
06 Dec 2016
Accepted
21 Jan 2017
First published
23 Jan 2017

Chem. Commun., 2017,53, 2048-2051

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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