Novel electrochemical pathway to fluoroalkyl phosphines and phosphine oxides

• Organofluorine phosphines are obtained from white phosphorous under electrocatalysis.
• The procedure is applicable for partly fluorinated and fully fluorinated phosphines.
• Electrocatalytic coupling with diphenylchlorophosphine leads to fluorinated product.
• Electrochemically generated bypiridine nickel (0) complex serves as catalyst.
• Available fluoroalkyl iodides are used as the fluoroalkyl sources.

Novel versatile electrocatalytic route for obtaining fluoroalkylated phosphines and phosphine oxides from white phosphorous or diphenylchlorophosphine is discussed. This process occurs under electrochemical generation of nickel complexes in low oxidation state during undivided electrolysis of organofluorine iodides and phosphorous-containing substrate in mild conditions without supporting electrolyte.

The electrochemical joint reduction of fluoroalkyl iodides in presence of 2,2′-bipyridine nickel dibromide with white phosphorous or diphenylchlorophosphine leads effectively to fluoroalkyl phosphines in mild conditions.Figure optionsDownload as PowerPoint slide