Pyridyl Radical Cation for C-H Amination of Arenes

被引：95

作者：

Rossler, Simon L. ^{[1
]}

Jelier, Benson J. ^{[2
]}

Tripet, Pascal F. ^{[2
]}

Shemet, Andrej ^{[1
]}

Jeschke, Gunnar ^{[3
]}

Togni, Antonio ^{[2
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Lab Organ Chem, Vladimir Prelog Weg, CH-8093 Zurich, Switzerland

[2] Swiss Fed Inst Technol, Lab Inorgan Chem, Vladimir Prelog Weg, CH-8093 Zurich, Switzerland

[3] Swiss Fed Inst Technol, Lab Phys Chem, Vladimir Prelog Weg, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 02期

基金：

加拿大自然科学与工程研究理事会;

关键词：

amination; late-stage functionalization; photoredox catalysis; pyridyl radical cation; radical mechanism; AROMATIC EDA COMPLEXES; PRIMARY AMINES; AMIDATION; IMIDATION; HETEROARENES; SUBSTITUTION; GENERATION; SALTS; PRECURSORS; REACTIVITY;

D O I：

10.1002/anie.201810261

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp(2))-H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N-X pyridinium reagents mediated by visible light.

引用

页码：526 / 531

页数：6

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