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Merging Photoinduced Electron Transfer with Hydrogen Atom Transfer: Formal β-C(sp<sup>3</sup>)–H Pyridination of Carbonyls

Jian Li, Jun Xu, Binbin Chen, Qing Pang, Jiabin Shen, Kai Wang, Pengfei Zhang

2025The Journal of Organic Chemistry22 citationsDOI

Abstract

In this study, a novel approach that combines photoinduced electron transfer (ET) with hydrogen atom transfer (HAT) has been introduced for the selective β-C(sp 3 )–H pyridination of carbonyl compounds. This method is notable for its absence of transition metals and its ability to function under benign reaction conditions, resulting in a range of pyridinated carbonyl derivatives with consistently moderate to good yields. The significance of this technique is further underscored by its potential for the late-stage functionalization of pharmaceutically significant molecules. Mechanistic investigations confirmed that the reaction proceeds via a radical-mediated pathway.

Topics & Concepts

Hydrogen atomChemistryElectron transferMoleculePhotoinduced electron transferHydrogenPhotochemistryAtom (system on chip)Proton-coupled electron transferSurface modificationHydrogen moleculeComputational chemistryOrganic chemistryPhysical chemistryGroup (periodic table)Embedded systemComputer scienceRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Merging Photoinduced Electron Transfer with Hydrogen Atom Transfer: Formal β-C(sp<sup>3</sup>)–H Pyridination of Carbonyls | Litcius