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

Swern Oxidation Oxidation of Secondary Alcohol to Ketone Claisen Condensation (Ethyl Acetate) Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Condensation Polymerization (Nylon 6,6) Cope Rearrangement Epoxidation of Alkenes (mCPBA)

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).