Cyclic Hypervalent Iodine Reagents as a Bifunctional Platform for Benzylic C–H Oxidation via Dual Oxidative Radical–Polar Crossover
Jiaxin He , Haofeng Shi , Jialiang Wu , Kaiyue Yang , Dan Xiao , Lingzhi Xu , Yunfei Du
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) : 3405 -3413.
The selective functionalization of unactivated benzylic C–H bonds in arenes and N-heteroarenes remains a pivotal challenge in synthetic chemistry, particularly for constructing oxygen-containing functional groups with precision. Herein, we present an efficient photoredox-catalysis strategy for the selective oxidation of benzylic C(sp3)–H bonds in both aromatic and N-heteroaromatic systems. This protocol employed cyclic hypervalent iodine reagents as a bifunctional platform functioning as hydrogen atom transfer (HAT) agent or radical precursor to facilitate the dual oxidative radical–polar crossover (ORPC) process under mild conditions, wherein water served as either a nucleophilic oxygen donor or quenching agent to initiate the oxidation process.
Oxidation / Photocatalysis / Cyclic hypervalent iodine reagents / Bifunctional platform / Oxidative radical–polar crossover / Hydrogen atom transfer / Radical addition / Carbonyl compounds
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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