Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two‐dimensional covalent organic frameworks (2D‐COFs) have become promising heterogenous photocatalysts in visible‐light‐driven organic transformations. Herein, a visible‐light‐driven selective aerobic oxidation of various small organic molecules by using 2D‐COFs as the photocatalyst was...

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Bibliographic Details
Published in:Chemistry : a European journal 2021-05, Vol.27 (28), p.7738-7744
Main Authors: Liu, Shuyang, Tian, Miao, Bu, Xiubin, Tian, Hua, Yang, Xiaobo
Format: Article
Language:English
Subjects:
aerobic oxidation
Amides
Chemistry
covalent organic frameworks
Functional groups
Heterocyclic compounds
Hydrazones
Modafinil
Mustard gas
Organic chemistry
Oxidation
Oxygen
Photocatalysis
Photocatalysts
Quinolones
Recyclability
small organic molecules
Spectroscopy
Sulfoxides
Sustainability
visible-light-driven
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Summary:Photoactive two‐dimensional covalent organic frameworks (2D‐COFs) have become promising heterogenous photocatalysts in visible‐light‐driven organic transformations. Herein, a visible‐light‐driven selective aerobic oxidation of various small organic molecules by using 2D‐COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone‐based 2D‐COF‐1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2‐chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale‐up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D‐COF‐1 in photocatalytic cycle. COFs in photocatalytic oxidation of organics: Hydrazone‐based 2D‐COF‐1 offers a fascinating alternative photocatalyst for visible‐light‐driven selective aerobic oxidation of valuable small organics such as amines, ethers, thioethers and pyridinium salts. By means of its superior photocatalytic ability in molecular oxygen activation and inherent heterogenous nature, the present protocol exhibits impressive efficiency, selectivity and sustainability.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202100398