Photocatalytic Strategy to Realize N-Debenzylation via Aerobic Oxidation Catalyzed by 4CzIPN

被引：1

作者：

Wu Y. ^{[1
]}

Kang J. ^{[1
]}

Zhu H. ^{[2
]}

Bi M. ^{[1
]}

Li J. ^{[2
]}

Meng Q. ^{[2
]}

Lyu X. ^{[1
]}

Wu Z. ^{[1
]}

机构：

[1] State Key Laboratory of Fine Chemicals, Liaoning Provincial Key Laboratory of Chemical Safety and Emergency Technology, Department of Chemical Machinery and Safety, School of Chemical Engineering, Dalian University of Technology, Dalian

[2] State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian

来源：

ACS Sustainable Chemistry and Engineering | 2024年 / 12卷 / 17期

基金：

中国国家自然科学基金;

关键词：

4CzIPN; debenzylation; DFT; molecular oxygen; photocatalysis;

D O I：

10.1021/acssuschemeng.4c00202

中图分类号：

学科分类号：

摘要：

It is a great challenge to remove the N-benzyl protecting group selectively by photocatalytic aerobic oxidation because amides or imines are easily formed from the oxidation of N-benzylamine. In this study, a visible-light-induced debenzylation in yields of up to 88% was realized with a low catalytic loading of an organophotocatalyst [2 mol % 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN)] in the presence of air and HCl under mild conditions. Mechanisms involving two-electron-transfer processes, a proton-transfer process, and a hydrolysis process were proposed based on the experimental studies and density functional theory (DFT) calculations. Acetone plays an important role in the proton-transfer process to promote these debenzylations. © 2024 American Chemical Society.

引用

页码：6640 / 6647

页数：7

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