History
The original reaction by Tsutomu Mizoroki (1971) describes the coupling between iodobenzene and styrene to form stilbene in methanol at 120°C (autoclave) with potassium acetate base and palladium chloride catalysis. This work was an extension of earlier work by Fujiwara (1967) on the Pd(II)-mediated coupling of arenes (Ar–H) and alkenes and earlier work by Heck (1969) on the coupling of arylmercuric halides (ArHgCl) with alkenes using a stoichiometric amount of a palladium(II) species.
| Mizoroki 1971 |
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The 1972 Heck publication acknowledged the Mizoroki publication and detailed independently discovered work. The reaction conditions differ in catalyst used (palladium acetate) and catalyst loading (0.01 eq.), base used (a hindered amine) and lack of solvent.
| Heck 1972 |
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In these reactions the active catalyst Pd(0) (see reaction mechanism) is formed by Pd coordination to the alkene.
In 1974 Heck introduced phosphine ligands into the equation.
| Heck reaction 1974 phosphines |
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Read more about this topic: Heck Reaction
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