Heck Reaction—a transition metal-catalyzed coupling reaction

During the early 1970s, T. Mizoroki and R.F. Heck independently discovered that the reaction of aryl, benzyl, and styryl halides with alkenes at a high temperature in the presence of a hindered amine base and palladium catalyst resulted in the equivalent substituted alkenes. Today, the palladium-catalyzed arylation or alkenylation of alkenes is known as the Heck reaction, which since its discovery has become one of the most important synthetic tools for carbon-carbon bond formation.

One of the key features of the Heck reaction is that it tolerates a wide range of different functional groups such as esters, ethers, carboxylic acids, nitriles, phenols, and many others.

Despite its flexibility, the Heck reaction does have some drawbacks. For example, substrates cannot contain hydrogen atoms on their β-carbons, as corresponding organopalladium derivatives tend to undergo rapid β-hydride elimination to give alkenes.

During recent decades, several modifications have been introduced, such as the use of water-soluble catalysts and water as the solvent. The Heck reaction has been used in many synthetic reactions, including the synthesis of the potent anticancer agent lasiodiplodin and the antitumor agent ecteinascidin.