Electrochemical gold redox catalysis for selective oxidative arylation

Shuyao Zhang; Xiaohan Ye; Lukasz Wojtas; Wenyan Hao; Xiaodong Shi

doi:10.1016/j.gresc.2021.01.008

Electrochemical gold redox catalysis for selective oxidative arylation

Green Synth Catal. 2021 Feb;2(1):82-86. doi: 10.1016/j.gresc.2021.01.008. Epub 2021 Jan 31.

Authors

Shuyao Zhang¹, Xiaohan Ye¹, Lukasz Wojtas¹, Wenyan Hao², Xiaodong Shi¹

Affiliations

¹ Department of Chemistry, University of South Florida, Tampa, FL 33620, United States.
² College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.

Abstract

The combination of ArB(OH)₂ transmetallation with cationic gold(I) [LAu]⁺ and electrochemical anodic oxidation (EAO) approach was successfully developed for the preparation of Au^III-Ar intermediate for the first time. This in-situ generated aryl gold intermediate gave rapid and controllable transmetallation with ArB(OH)₂ or alkyne followed by reductive elimination to generate either di-aryl coupling or sp²-sp Sonogashira-type coupling products under mild conditions with no need of external oxidants, which significantly extended the versatility of electrochemical approach in promoting gold redox catalysis.

Keywords: Arylation; Electrochemistry; Gold redox catalysis; Oxidative coupling.

Grants and funding

R01 GM120240/GM/NIGMS NIH HHS/United States