Photoinitiated Multicomponent Anti-Markovnikov Alkoxylation over Graphene Oxide

The development of graphene oxide-based heterogeneous materials with an economical and environmentally-friendly manner has the potential to facilitate many important organic transformations but proves to have few relevant reported reactions. Herein, we explore the synergistic role of catalytic systems driven by graphene oxide and visible light that form nucleophilic alkoxyl radical intermediates, which enable an anti-Markovnikov addition exclusively to the terminal alkenes, and then the produced benzyl radicals are subsequently added with N-methylquinoxalones. This photoinduced cascade radical difunctionalization of olefins offers a concise and applicable protocol for constructing alkoxyl-substituted N-methylquinoxalones.

Automated summary

This study investigates the synergistic role of catalytic systems driven by graphene oxide and visible light, enabling anti-Markovnikov addition to terminal alkenes and subsequent difunctionalization with N-methylquinoxalones. The photoinduced cascade radical difunctionalization of olefins provides a concise and applicable protocol for constructing alkoxyl-substituted N-methylquinoxalones.