Tuning O2 Reactivity through Synergistic Photo/Copper Catalysis: Direct Synthesis of 4-Aryl tetralones via Cyclodimerization-Oxygenation of Styrenes

Xu Zhang; Hong Yi; Yi Luo; Aiwen Lei

doi:10.1002/asia.201600758

Tuning O2 Reactivity through Synergistic Photo/Copper Catalysis: Direct Synthesis of 4-Aryl tetralones via Cyclodimerization-Oxygenation of Styrenes

Chem Asian J. 2016 Aug 5;11(15):2117-20. doi: 10.1002/asia.201600758. Epub 2016 Jul 8.

Authors

Xu Zhang¹, Hong Yi¹, Yi Luo¹, Aiwen Lei^{2

3}

Affiliations

¹ College of Chemistry and Molecular Sciences, Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072, P. R. China.
² College of Chemistry and Molecular Sciences, Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072, P. R. China. aiwenlei@whu.edu.cn.
³ National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, Jiangxi, P. R. China. aiwenlei@whu.edu.cn.

PMID: 27319756
DOI: 10.1002/asia.201600758

Abstract

A transformation is presented that enables chemists to construct 4-aryl tetralones via visible-light-induced cyclodimerization-oxygenation of styrene under very mild conditions. Adding a catalytic amount of CuOAc obviously improves the yield. A mechanistic study reveals that the photoredox catalyst played the role of activating O2 while Cu affected the reactivity of reactive oxygen species (ROS).

Keywords: O2 activation; copper catalysis; photoredox catalysis; superoxide radical anion.