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Transition metal-free stereospecific access to (E)-(1-fluoro-2-arylvinyl)phosphine borane complexes
Kevin Rousée1, Xavier Pannecoucke1, Annie-Claude Gaumont2
1Normandie Univ., INSA Rouen, UNIROUEN, CNRS, COBRA, 76000 Rouen, France. samuel.couve-bonnaire@insa-rouen.fr.
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.
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