Selective α-oxidation of amides visible-light-driven iron catalysis.

Org Biomol Chem

Institute of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China.

Published: February 2024

Hydroxyl radicals (˙OH) as one of the highly reactive species can react unselectively with a wide range of chemicals. The ˙OH radicals are typically generated under harsh conditions. Herein, we report hydroxyl radical-induced selective -α C(sp)-H bond oxidation of amides under greener and mild conditions an Fe(NO)·9HO catalyst inner sphere pathway upon irradiation with a 30 W blue LED light strip ( = 455 nm) using NaBrO as the oxidant. This protocol exhibited high chemoselectivity and excellent functional group tolerance. A preliminary mechanism investigation demonstrated that the iron catalyst afforded hydroxyl radicals the visible-light-induced homolysis (VLIH) of iron complexes followed by a hydrogen atom transfer (HAT) process to realize this transformation.

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Source
http://dx.doi.org/10.1039/d3ob01984eDOI Listing

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