Science of Synthesis

Shen, Q.; Guo, F.; Hartwig, J. F., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 2, 173.

General Introduction

Diarylamines containing at least one hetaryl group represent a privileged structural motif because of their prevalence in natural products, pharmacological agents, fine chemicals, dyes, and polymeric materials.[‌1‌,‌2‌] Classical methods for the preparation of this family of amines through nucleophilic aromatic substitution (SNAr) typically produce only modest yields of the desired hetarylamines, often have limited substrate scope, and/or require high temperatures because of the modest nucleophilicity of the aryl- or hetarylamine nucleophile. The amination of aryl electrophiles catalyzed by transition-metal complexes, such as the Buchwald–Hartwig reaction,[‌3‌,‌4‌] the modified copper-catalyzed Ullmann–Goldberg reaction,[‌5‌–‌7‌] or the oxidative amination of aryl nucleophiles by the Chan–Lam reaction,[‌8‌,‌9‌] provide new approaches to the synthesis of arylamines. However, the amination of hetaryl electrophiles is much more challenging than the amination of aryl electrophiles.

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References