Photocatalyst-Free Access to α‑Arylethanone Oximes Enabled by Sequential HAT/SET of Aryl Iodides with TBN and Alkenes

Abstract

Herein, we report a regioselective aryl-oximation of alkenes that proceeds without a photocatalyst. This method exploits a hydrogen atom transfer (HAT)/ single-electron transfer (SET) relay sequence to activate the aryl iodide, employing tert-butyl nitrite (TBN) as a dual-function reagent that serves as both the HAT agent and the oxime source. This transformation utilizes cost-effective, readily available formate salts as SET reagents under simple conditions, featuring a broad substrate scope and excellent functional group tolerance to provide a novel pathway for oxime synthesis.