摘要：Department of Chemistry and ChemicalBiology, Cornell University, Ithaca, New York 14853, United States;

转自：康龙化成

Oxoammonium-Catalyzed Oxidation ofN‑Substituted Amines

JonasRein, Bartosz Górski, Yukun Cheng, Zhen Lei, Frederic Buono, and Song Lin*

Department of Chemistry and ChemicalBiology, Cornell University, Ithaca, New York 14853, United States;

Chemical Development U.S., BoehringerIngelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States

—J.Am. Chem. Soc., 2024, DOI：https://doi.org/10.1021/jacs.4c11758

Recommended by Yuting Gao_MC3

KEYWORDS: oxidation(反应类型),N-substituted amines (原料),amides (产物),C(sp2)-O (成键类型),m-CPBA (试剂),oxoammonium (催化剂)

ABSTRACT: Wereport the development of oxoammonium-catalyzed oxidation of N-substitutedamines via a hydride transfer mechanism. Steric and electronic tuning ofcatalyst led to complementary sets of conditions that can oxidize a broad scopeof carbamates, sulfonamides, ureas, andamides into the corresponding imides. The reaction was further demonstrated ona 100-g scale using a continuous flow setup.

Background

Substrates scope

Schematicof the continuous flow setup for preparative-scale synthesis

The Group of Prof. SongLin has developed an oxoammonium-catalyzed chemoselective oxidation of N-substituted amines, which exhibits a broad substrate scope andcan be readily scaled using continuous flow. This reaction undergoes a hydridetransfer mechanism, which remains underexplored in C−H functionalization butprovides complementary reactivity and selectivity to widely establishedradical-based approaches.

来源：新浪财经