Heck Reaction (Palladium-Catalyzed Coupling)

ArX + CH2=CHR → ArCH=CHR + HX

概述

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.

日常示例

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

工业重要性

赫克反应是构建碳-碳键的重要方法，广泛用于制药行业（如萘普生、阿托伐他汀中间体）、液晶材料和精细化工品合成，2010年诺贝尔化学奖表彰了其发现者。

属性

类型
Organic
可逆
否
能量
放热
ΔH
-35.0 kJ/mol
催化剂
Pd(OAc)₂ / PPh₃

相关反应

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).