Exploring N-centered umpolung reactivity in photoredox-catalyzed amidation with an α-iminoester

被引：2

作者：

Mistry, Parag ^{[1
]}

Das, Subhankar ^{[1
]}

Patra, Rik ^{[1
]}

Chatterjee, Indranil ^{[1
]}

机构：

[1] Indian Inst Technol Ropar, Dept Chem, Nangal Rd, Rupnagar 140001, Punjab, India

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 23期

关键词：

CASCADE REACTIONS; ALKYLATION; ACIDS; CONSTRUCTION; ARYLATION; ACYLATION; RADICALS; IMINES;

D O I：

10.1039/d4qo01515k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of amides and their derivatives has gained significant attention from the scientific community in recent decades due to the presence of amide moieties in many bioactive organic molecules. Pursuing sustainable chemistry using cost-effective starting materials under mild reaction conditions is intriguing and challenging. In this context, we present a method for the direct synthesis of amides from alpha-keto acids and alpha-iminoesters. This approach employs an Ir-based photocatalyst to enable redox-neutral C-N bond formation at room temperature through N-center umpolung chemistry. This straightforward protocol is compatible with a broad range of functional groups, allowing for the efficient production of amides from aromatic keto acids and imines as coupling partners in an atom-economical manner. Visible light photoredox catalysis facilitates the synthesis of amide derivatives from alpha-ketoacids and alpha-iminoesters, unveiling the N-centered umpolung reactivity of the imine functionality in a redox-neutral and atom-economical fashion.

引用

页码：6778 / 6783

页数：6