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

Epoxidation of Alkenes (mCPBA) Swern Oxidation Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Dehydration of Ethanol

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).