Copper(I)-Mediated C-N/C-C Bond-Forming Reaction With Tetrafluoroethylene For The Synthesis Of N-Fluoroalkyl Heteroarenes Via An Azacupration/Coupling Mechanism

A novel copper(I)-mediated C-N/C-C bond-forming reaction involving tetrafluoroethylene (TFE), imidazolide or benz-imidazolide salts, and aryl iodides has been developed. This three-component coupling reaction can provide highly functionalized N-fluoroalkyl heteroaromatic compounds in up to 98% yield via a one-pot procedure. The azacupration of TFE with the copper(I) imidazolide species to afford the fluoroalkylcopper(I) complex is the key process in the transformation.