Highly Efficient Pd-Catalyzed Oxidative sp²-sp² C-C Bond Formation

Significance

Herein, the authors report a novel approach to the formation of sp²-sp² C-C bonds, based on the oxidative Pd(II) catalysis. This method represents an alternative to the common Heck or Suzuki reactions, especially in the cases of polysubstituted olefins, for which these methods are less suitable. It represents an example of an oxidative addition of a carbon nucleophile to an alkene. Alkenyl- and arylboronic acids can be coupled in the presence of O₂ and a Pd catalyst with various alkenes, giving dienes or substituted styrenes in excellent yields. Inexpensive phenanthrolines are used as ligands for palladium. In many cases, this method outperforms the known ones for a new C-C bond formation.