Stereoselective C-C Oxidative Coupling Reactions Photocatalyzed by Zwitterionic Ligand Capped CsPbBr3 Perovskite Quantum Dots

Angew Chem Int Ed Engl. 2020 Dec 7;59(50):22563-22569. doi: 10.1002/anie.202007520. Epub 2020 Oct 8.

Abstract

Semiconductor quantum dots (QDs) have attracted tremendous attention in the field of photocatalysis, owing to their superior optoelectronic properties for photocatalytic reactions, including high absorption coefficients and long photogenerated carrier lifetimes. Herein, by choosing 2-(3,4-dimethoxyphenyl)-3-oxobutanenitrile as a model substrate, we demonstrate that the stereoselective (>99 %) C-C oxidative coupling reaction can be realized with a high product yield (99 %) using zwitterionic ligand capped CsPbBr3 perovskite QDs under visible light illumination. The reaction can be generalized to different starting materials with various substituents on the phenyl ring and varied functional moieties, producing stereoselective dl-isomers. A radical mediated reaction pathway has been proposed. Our study provides a new way of stereoselective C-C oxidative coupling via a photocatalytic means using specially designed perovskite QDs.

Keywords: CsPbBr3; C−C coupling; perovskite QDs; photocatalysis; stereoselectivity.