Photoinitiated Multicomponent Anti-Markovnikov Alkoxylation over Graphene Oxide.

Liang Nie,Ming Yang,Fan Li,Liangxian Liu,Zhiyang Yao,Linyi Zhou,Xiangjun Peng,Haiping He,Qing Huang,Jian Hu

doi:10.3390/molecules27020475

Liang Nie, Ming Yang + Show 8 more

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https://doi.org/10.3390/molecules27020475

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Abstract

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.

Highlights

Alkoxylation over Graphene Oxide.The graphene oxide (GO), as one of the popular carbocatalysts with two-dimensional honeycomb structures, has giant π-conjugated systems, unpaired electrons and several oxygen-containing function groups, such as hydroxy, epoxide, carbonyl and carboxyl groups, which have the acidic, nucleophilic and oxidized capabilities [1–10]
The superior electrical conductivity, high specific surface area and excellent optical transmittance impart to GO crucial properties such as: a template for anchor active species to metal or photocatalysts, and synergistic interactions between them resulting in improved yield [11–14]
GO-based photocatalysts offer prospective applications to associate with photoenergy conversion, and the exploration of different approaches in organic transformations have been improved by GO-based photocatalytic redox processes

Summary

Introduction

Alkoxylation over Graphene Oxide.The graphene oxide (GO), as one of the popular carbocatalysts with two-dimensional honeycomb structures, has giant π-conjugated systems, unpaired electrons and several oxygen-containing function groups, such as hydroxy, epoxide, carbonyl and carboxyl groups, which have the acidic, nucleophilic and oxidized capabilities [1–10]. The superior electrical conductivity, high specific surface area and excellent optical transmittance impart to GO crucial properties such as: a template for anchor active species to metal or photocatalysts, and synergistic interactions between them resulting in improved yield [11–14]. Given such a situation, GO-based photocatalysts offer prospective applications to associate with photoenergy conversion, and the exploration of different approaches in organic transformations have been improved by GO-based photocatalytic redox processes.

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