A Single‐COF Photocatalytic System for One‐Pot Oxygen Reduction Coupled Ammoximation of Cyclic Ketones

ABSTRACT Photocatalytic oxygen reduction over covalent organic frameworks (COFs) has been extensively studied for H 2 O 2 production, but the in situ utilization of oxygen reduction reaction (ORR) intermediates in chemical synthesis remains underexplored. Herein, two porphyrin‐based polyimide COFs, IMCOF‐1 and IMCOF‐2, are reported as photocatalysts for the one‐pot ORR‐coupled ammoximation of cyclic ketones using O 2 and NH 4 OAc. Under light irradiation, IMCOF‐1 achieves a cyclohexanone oxime formation rate of 18.55 mmol g −1 h −1 and is effective for several other cyclic ketones. Mechanistic investigations reveal that photoinduced electron transfer from the porphyrin units to the electron‐deficient imide moieties promotes charge separation and activates O 2 at the carbonyl sites. The resulting surface‐bound *OOH intermediates are proposed to participate in ammonia oxidation and subsequent NH 2 OH formation, which then condenses with cyclic ketones to yield the corresponding oximes. In contrast to stepwise systems that first accumulate H 2 O 2 before ammoximation, the present one‐pot strategy enables the in situ utilization of oxygen‐derived reactive intermediates without requiring substantial bulk H 2 O 2 pre‐accumulation, eliminating the need for H 2 O 2 isolation, storage, and transport, thereby improving safety and atom economy while maintaining high selectivity. This work demonstrates the potential of directly harnessing ORR‐derived intermediates for the light‐driven synthesis of value‐added nitrogen‐containing chemicals.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2026-11-08
DOI
https://doi.org/10.1002/anie.2045143
Primary Topic
Covalent Organic Framework Applications
Type
article
Field-Weighted Citation Impact
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article

A Single‐COF Photocatalytic System for One‐Pot Oxygen Reduction Coupled Ammoximation of Cyclic Ketones

Xueshan Xing, Qianrong Fang, Yujie Wang, Jian Liu et al.
5 links
Angewandte Chemie International Edition
Covalent Organic Framework Applications
article

A Single‐COF Photocatalytic System for One‐Pot Oxygen Reduction Coupled Ammoximation of Cyclic Ketones

Xueshan Xing, Qianrong Fang, Yujie Wang, Jian Liu, Chuanbao Jiao, Ruipeng Li, Jiashuai Teng, Hui Li, Jiali Li
article en

Abstract

ABSTRACT Photocatalytic oxygen reduction over covalent organic frameworks (COFs) has been extensively studied for H 2 O 2 production, but the in situ utilization of oxygen reduction reaction (ORR) intermediates in chemical synthesis remains underexplored. Herein, two porphyrin‐based polyimide COFs, IMCOF‐1 and IMCOF‐2, are reported as photocatalysts for the one‐pot ORR‐coupled ammoximation of cyclic ketones using O 2 and NH 4 OAc. Under light irradiation, IMCOF‐1 achieves a cyclohexanone oxime formation rate of 18.55 mmol g −1 h −1 and is effective for several other cyclic ketones. Mechanistic investigations reveal that photoinduced electron transfer from the porphyrin units to the electron‐deficient imide moieties promotes charge separation and activates O 2 at the carbonyl sites. The resulting surface‐bound *OOH intermediates are proposed to participate in ammonia oxidation and subsequent NH 2 OH formation, which then condenses with cyclic ketones to yield the corresponding oximes. In contrast to stepwise systems that first accumulate H 2 O 2 before ammoximation, the present one‐pot strategy enables the in situ utilization of oxygen‐derived reactive intermediates without requiring substantial bulk H 2 O 2 pre‐accumulation, eliminating the need for H 2 O 2 isolation, storage, and transport, thereby improving safety and atom economy while maintaining high selectivity. This work demonstrates the potential of directly harnessing ORR‐derived intermediates for the light‐driven synthesis of value‐added nitrogen‐containing chemicals.

Angewandte Chemie International Edition
Jilin University (CN), Inner Mongolia University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Inner Mongolia, State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Higher Education Discipline Innovation Project, National Key Research and Development Program of China
Responsible consumption and production
Covalent Organic Framework Applications
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