Heck Reaction (Palladium-Catalyzed Coupling)

ArX + CH2=CHR → ArCH=CHR + HX

개요

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.

일상 속 예시

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

산업적 중요성

제약, 농약, 재료 과학 분야에서 복잡한 유기 분자의 C-C 결합 형성에 필수적입니다. 항암제, 항생제 등 의약품 합성의 핵심 반응으로 활용됩니다.

성질

유형
Organic
가역 반응
아니오
에너지
발열
ΔH
-35.0 kJ/mol
촉매
Pd(OAc)₂ / PPh₃

관련 반응

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).