Transition metal-free stereospecific access to (E)-(1-fluoro-2-arylvinyl)phosphine borane complexes. Issue 12 (27th January 2017)

• Record Type: Journal Article
• Authors: Rousée, Kevin; Pannecoucke, Xavier; Gaumont, Annie-Claude; Lohier, Jean-François; Morlet-Savary, Fabrice; Lalevée, Jacques; Bouillon, Jean-Philippe; Couve-Bonnaire, Samuel; Lakhdar, Sami
• Is Part Of: Chemical communications. Volume 53:Issue 12(2017)
• Page Start: 2048
• Page End: 2051
• Publication Date: 2017-01-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc09673e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Synthesis of ( E )-(1-fluoro-2-arylvinyl)phosphine boranes has been achieved under metal-free conditions. 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 SRN 1 mechanism. The formation of the fluorinated vinyl radical has been evidenced by electron paramagnetic resonance (EPR) experiment.