Heck reaction
| Heck reaction | |
|---|---|
| Named after | Richard F. Heck |
| Reaction type | Coupling reaction |
| Identifiers | |
| Organic Chemistry Portal | heck-reaction |
| RSC ontology ID | RXNO:0000024 |
The Heck reaction (also called the Mizoroki-Heck reaction) is the chemical reaction of an unsaturated halide (or triflate) with an alkene in the presence of a base and a palladium catalyst (or palladium nanomaterial-based catalyst) to form a substituted alkene. It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and Akira Suzuki, for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed cross-coupling reactions. The Heck reaction is of great importance, as it allows one to do substitution reactions on planar sp2-hybridized carbon atoms.
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 hydrogen 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.
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