Heck Reaction (Palladium-Catalyzed Coupling)

ArX + CH₂=CHR → ArCH=CHR + HX

Tổng quan

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.

Ví dụ thực tế

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

Tầm quan trọng công nghiệp

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

Tính chất

Loại: Organic
Thuận nghịch: Không
Năng lượng: Tỏa nhiệt
ΔH: -35,0 kJ/mol
Chất xúc tác: Pd(OAc)₂ / PPh₃

Phản ứng liên quan

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).