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Stereoselective C−C Oxidative Coupling Reactions Photocatalyzed by Zwitterionic Ligand Capped CsPbBr<sub>3</sub> Perovskite Quantum Dots

Yucheng Yuan, Hua Zhu, Katie Hills‐Kimball, Tong Cai, Wenwu Shi, Zichao Wei, Hanjun Yang, Yolanda Candler, Ping Wang, Jie He, Ou Chen

2020Angewandte Chemie International Edition110 citationsDOI

Abstract

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 (&gt;99 %) C−C oxidative coupling reaction can be realized with a high product yield (99 %) using zwitterionic ligand capped CsPbBr 3 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.

Topics & Concepts

Perovskite (structure)Quantum dotLigand (biochemistry)Coupling (piping)StereoselectivityOxidative coupling of methaneChemistryMaterials sciencePhotochemistryPhysicsNanotechnologyCatalysisCrystallographyOrganic chemistryBiochemistryReceptorMetallurgyPerovskite Materials and ApplicationsQuantum Dots Synthesis And PropertiesSulfur-Based Synthesis Techniques
Stereoselective C−C Oxidative Coupling Reactions Photocatalyzed by Zwitterionic Ligand Capped CsPbBr<sub>3</sub> Perovskite Quantum Dots | Litcius