Heck Reaction (Palladium-Catalyzed Coupling)

ArX + CH2=CHR → ArCH=CHR + HX

概要

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.

日常の例

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

産業上の重要性

ヘック反応は医薬品合成、農薬製造、有機エレクトロニクス材料の製造に利用される。鈴木・根岸カップリングとともにパラジウム触媒クロスカップリング反応の三大柱の一つ。

特性

タイプ
Organic
可逆的
いいえ
エネルギー
発熱性
ΔH
-35.0 kJ/mol
触媒
Pd(OAc)₂ / PPh₃

関連する反応

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).