Nucleophilic Amination of Aryl Halides with an Azanide Surrogate

被引：0

作者：

Cooper, Bradley D. ^{[1
]}

Harris, Thomas D. ^{[1
]}

Lim, Ethan R. X. ^{[1
]}

Hooper, Katherine A. ^{[1
]}

Whitehead, George F. S. ^{[1
]}

Carney, Jonathan R. ^{[2
]}

James, Michael J. ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Oxford Rd, Manchester M13 9PL, England

[2] AstraZeneca, Chem Dev Pharmaceut Technol & Dev Operat, Macclesfield SK10 2NA, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2025年 / 31卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

Azanide; Surrogate; Nucleophilic substitution; Amines; Transition-metal-free; PALLADIUM-CATALYZED AMINATION; C-H AMINATION; AMMONIA; POTASSIUM; ARYLAMINES; CHLORIDES;

D O I：

10.1002/chem.202403952

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the development of an azanide (-NH2) surrogate which enables the facile conversion of electron-deficient (hetero)aryl halides into primary N-aryl amines under transition-metal-free conditions. The designed amidine reagent is easy to prepare, bench stable, and undergoes facile N-arylation under basic conditions at 40 degrees C. Intermediate N-aryl amidines are readily cleaved to form N-aryl amines in situ through hydrolysis or base-promoted elimination. The developed surrogate is a safer and more selective alternative to existing anionic N-nucleophiles, such as alkali metal amides or azide salts.

引用

页数：6

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