Regiospecific Syn Addition of (Polyfluoroaryl)copper Reagents to Fluorinated Acetylenes: Preparation and Subsequent Functionalization of Internal Vinylcopper Reagents

Article abstract of DOI:10.1021/jo00068a041

(Pentafluorophenyl)copper (C6F5Cu) can be prepared from a metathesis reaction between C6F5CdX (X = Br or C6F5) and CuY (Y = Cl or Br).The arylcopper reagent undergoes a stereo- and regiospecific syn addition to fluorinated alkynes, which results in the corresponding internal alkenylcopper intermediate.This vinylcopper reagent can be subsequently functionalized with a variety of electrophiles, including aryl, alkyl, allyl, and acyl halides, to afford tetrasubstituted fluoroalkenes.The para-substituted arylcopper analogs also successfully undergo the addition reaction.