Heck Reaction (Palladium-Catalyzed Coupling)

ArX + CH₂=CHR → ArCH=CHR + HX

Visão geral

The Heck reaction couples an aryl or vinyl halide with an alkene using a palladium catalyst and base. The mechanism involves oxidative addition of ArX to Pd(0), syn-migratory insertion into the alkene, and beta-hydride elimination to give the substituted alkene. Richard Heck shared the 2010 Nobel Prize.

Exemplo do cotidiano

The anti-inflammatory drug naproxen and the sunscreen ingredient octyl methoxycinnamate are synthesized using the Heck reaction.

Importância industrial

A reação de Heck é utilizada na síntese farmacêutica, produção de agroquímicos e síntese de materiais. Richard Heck, Ei-ichi Negishi e Akira Suzuki partilharam o Prémio Nobel da Química em 2010 pelo desenvolvimento de acoplamentos cruzados catalisados por paládio.

Propriedades

Tipo: Organic
Reversível: Não
Energia: Exotérmico
ΔH: -35,0 kJ/mol
Catalisador: Pd(OAc)₂ / PPh₃

Reações relacionadas

Swern Oxidation Oxidation of Secondary Alcohol to Ketone Claisen Condensation (Ethyl Acetate) Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Condensation Polymerization (Nylon 6,6) Cope Rearrangement Epoxidation of Alkenes (mCPBA)

Frequently Asked Questions

What is the equation for Heck Reaction (Palladium-Catalyzed Coupling)?

The balanced equation is: ArX + CH₂=CHR → ArCH=CHR + HX.

What type of reaction is Heck Reaction (Palladium-Catalyzed Coupling)?

Heck Reaction (Palladium-Catalyzed Coupling) is a organic reaction.

Is Heck Reaction (Palladium-Catalyzed Coupling) exothermic or endothermic?

Heck Reaction (Palladium-Catalyzed Coupling) is exothermic (releases energy). The enthalpy change (ΔH) is -35.0 kJ/mol.

What conditions are needed for Heck Reaction (Palladium-Catalyzed Coupling)?

This reaction requires a catalyst (Pd(OAc)₂ / PPh₃).