Issue 41, 2025

Photoinduced and proton-activated N-heteroarene-catalyzed dioxygen activation for benzylic and allylic oxidation

Abstract

Photo-oxygenation has emerged as a promising strategy for the efficient synthesis of high-value-added carbonyl compounds through direct elaboration of ubiquitous C–H bonds. However, the conventional methods relying on superstoichiometric oxidants, expensive transition metals, or organic photocatalysts with cumbersome syntheses in light-driven oxygenation processes are often deemed economically unfeasible, thus detracting from their potential application in industry. Herein, we present an organic photosensitizer based on a “proton-activation” mode, which could be assembled via the simple protonation of commercially available N-heteroarenes with an acid. Upon visible-light irradiation, the proton-activated N-heteroarene features a key energy-transfer process with molecular dioxygen in air to form singlet oxygen, facilitating diversified benzylic oxidation and allylic C–H bond oxidation. The observed diverse applicability suggests a generic platform for reaction simplification and accelerated synthetic discovery, which could enable broader applicability and accessibility in aerobic oxidation.

Graphical abstract: Photoinduced and proton-activated N-heteroarene-catalyzed dioxygen activation for benzylic and allylic oxidation

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Article information

Article type
Paper
Submitted
25 Jun 2025
Accepted
11 Sep 2025
First published
23 Sep 2025

Green Chem., 2025,27, 13051-13064

Photoinduced and proton-activated N-heteroarene-catalyzed dioxygen activation for benzylic and allylic oxidation

J. He, Y. Shi, H. Shi, J. Wu, K. Yang, D. Xiao, G. Huang and Y. Du, Green Chem., 2025, 27, 13051 DOI: 10.1039/D5GC03206G

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