Visible-Light-Promoted Iminyl-Radical Formation from Acyl Oximes: A Unified Approach to Pyridines, Quinolines, and Phenanthridines

被引：339

作者：

Jiang, Heng ^{[1
,2
]}

An, Xiaode ^{[1
,2
]}

Tong, Kun ^{[1
,2
]}

Zheng, Tianyi ^{[1
,2
]}

Zhang, Yan ^{[1
,2
]}

Yu, Shouyun ^{[1
,2
]}

机构：

[1] Nanjing Univ, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Peoples R China

[2] Nanjing Univ, Sch Chem & Chem Engn, Collaborat Innovat Ctr Chem Life Sci, Nanjing 210093, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 13期

基金：

中国国家自然科学基金;

关键词：

acyl oximes; N heteroarenes; iminyl radicals; photochemistry; visible light; C-H AMINATION; PHOTOREDOX CATALYSIS; REGIOSELECTIVE SYNTHESIS; REGIOSPECIFIC SYNTHESIS; OXIDATIVE CYCLIZATION; EFFICIENT SYNTHESIS; MODULAR SYNTHESIS; ALPHA-CARBOLINES; DERIVATIVES; ALKYNES;

D O I：

10.1002/anie.201411342

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac[Ir(ppy)(3)] as a photoredox catalyst, the acyl oximes were converted by 1e(-) reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-lightinduced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]-phenanthridine alkaloids.

引用

页码：4055 / 4059

页数：5

共 100 条

[1] N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].