Nickel-Catalyzed Formation of 1,3-Dienes via a Highly Selective Cross-Tetramerization of Tetrafluoroethylene, Styrenes, Alkynes, and Ethylene

In the presence of
a catalytic amount of Ni­(cod)2 (cod
= 1,5-cyclooctadiene) and PCy3 (Cy = cyclohexyl), the cross-tetramerization
of tetrafluoroethylene (TFE), alkynes, and ethylene occurred in a
highly selective manner to afford a variety of 1,3-dienes with a 3,3,4,4-tetrafluorobutyl
chain. In addition, a Ni(0)-catalyzed cross-tetramerization of TFE,
alkynes, ethylene, and styrenes was developed. These catalytic reactions
might proceed via partially fluorinated five- and seven-membered nickelacycle
key intermediates.