Oxime-Ether Group Transfer to Unpolarized C(sp3)─H Bonds via Light-Induced HAT Catalysis

In this study, we demonstrate an effective method for the direct conversion of alkane chemical feedstocks to valuable oxime-ethers through the functionalization of unpolarized C(sp³)─H bonds using light-induced HAT-catalysis. The process operates at room temperature, utilizing low catalyst loading (ppm level) and a reduced substrate-to-reagent ratio. Notably, the reaction can also be performed in sunlight, which makes the process further attractive toward sustainable synthesis of functionalized oxime-ethers. The process displays a broad substrate scope, rendering desired products with up to 90% yields. The reaction is shown to be scalable. Through a series of mechanistic control studies, a radical reaction pathway featuring HAT-induced C─H functionalization is implicated in the process.