Nickel-Catalyzed Three-Component Coupling Reaction of Tetrafluoroethylene and Aldehydes with Silanes via Oxa-Nickelacycles

The nickel-catalyzed synthesis of a variety of fluorine-containing silyl ethers from tetrafluoroethylene (TFE) and aldehydes with silanes in a selective manner is disclosed. Stoichiometric reactions revealed that the oxa-nickelacycle, which is generated upon oxidative cyclization of TFE and an aldehyde with Ni-0, is the key intermediate, whose molecular structure was confirmed by single-crystal X-ray diffraction analysis. In order to demonstrate the synthetic utility of this procedure, one of the reaction products was transformed into trifluorovinyl and organic silicon compounds via deprotonation with a Lewis base.