Heck Reaction (Palladium-Catalyzed Coupling)

ArX + CH₂=CHR → ArCH=CHR + HX

Overview

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.

Everyday Example

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

Industrial Importance

The Heck reaction is used in pharmaceutical synthesis, agrochemical production, and materials science for conjugated polymers.

Properties

Type: Organic
Reversible: No
Energy: Exothermic
ΔH: -35.0 kJ/mol
Catalyst: Pd(OAc)₂ / PPh₃

Related Reactions

Aldol Condensation of Acetaldehyde Amide Formation (Acetic Acid + Ammonia) Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Bromination of Ethylene Buchwald-Hartwig Amination Cannizzaro Reaction of Formaldehyde Catalytic Hydrogenation of Ethylene Claisen Condensation (Ethyl Acetate) Condensation Polymerization (Nylon 6,6)

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).