Buchwald-Hartwig Amination

ArBr + R2NH → ArNR2 + HBr

Descripción general

The Buchwald-Hartwig reaction couples aryl halides with amines using a palladium catalyst to form aryl C-N bonds. This transformation, developed independently by Stephen Buchwald and John Hartwig in the 1990s, solved a long-standing challenge in organic chemistry. The reaction tolerates diverse functional groups.

Ejemplo cotidiano

Many modern pharmaceuticals contain aryl amine bonds that were formed using this palladium-catalyzed coupling reaction.

Importancia industrial

La aminación de Buchwald-Hartwig se utiliza ampliamente en la química de procesos farmacéuticos y en la ciencia de materiales para semiconductores orgánicos y materiales para OLED.

Propiedades

Tipo
Organic
Reversible
No
Energía
Exotérmico
ΔH
-25,0 kJ/mol
Catalizador
Pd/BINAP

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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 Buchwald-Hartwig Amination?
The balanced equation is: ArBr + R₂NH → ArNR₂ + HBr.
What type of reaction is Buchwald-Hartwig Amination?
Buchwald-Hartwig Amination is a organic reaction.
Is Buchwald-Hartwig Amination exothermic or endothermic?
Buchwald-Hartwig Amination is exothermic (releases energy). The enthalpy change (ΔH) is -25.0 kJ/mol.
What conditions are needed for Buchwald-Hartwig Amination?
This reaction requires a catalyst (Pd/BINAP).