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Heck Reaction

Heck reaction   Named Reactions in Organic Synthesis
Reaction category:
Transition metal-catalyzed couplings

Other featured reactions:

 

During the early 1970’s 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. Nowadays the palladium catalysed arylation or alkenylation of alkenes is known as the Heck reaction and since it’s 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 organo-palladium 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 as a solvent utilizing water soluble catalysts. The Heck reaction has been used in many synthetic routes including the potent anticancer agent lasiodiplodin and the antitumor agent Ecteinascidin.





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Other reaction categories:

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle formation

Oxidation

Reactions involving carbonyl compounds

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Some relevant Alfa Aesar products for the Heck reaction:
Allylpalladium(II) chloride dimer, Pd 56.0% min
Bis(dibenzylideneacetone)palladium(0)
Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II), Pd 16.3%
trans-Dichlorobis(triphenylphosphine)palladium(II), Pd 14.0% min
trans-Dichlorobis(triphenylphosphine)palladium(II), Premion®, 99.95% (metals basis), Pd 14.7% min
Palladium(II) acetate, Pd 45.9-48.4%
Tetrakis(triphenylphosphine)palladium(0), 99.8% (metals basis), Pd 9% min
Triethylamine, 99+% Tris(dibenzylideneacetone)dipalladium(0), complex with chloroform, Pd 20.6%

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