Heck Reaction

The Heck reaction (also called the Mizoroki-Heck reaction) is the chemical reaction of an unsaturated halide (or triflate) with an alkene and a base and palladium catalyst or palladium nanomaterial-based catalyst to form a substituted alkene. Together with the other palladium-catalyzed cross-coupling reactions, this reaction is of great importance, as it allows one to do substitution reactions on planar centers. It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry for the discovery and development of this reaction.

The reaction is performed in the presence of an organopalladium catalyst. The halide (Br, Cl) or triflate is an aryl, benzyl, or vinyl compound and the alkene contains at least one proton and is often electron-deficient such as acrylate ester or an acrylonitrile.The catalyst can be tetrakis(triphenylphosphine)palladium(0), palladium chloride or palladium(II) acetate. The ligand is triphenylphosphine, PHOX or BINAP. The base is triethylamine, potassium carbonate or sodium acetate.

Several reviews have been published.