4.8 Article

Stereoselective C-C Oxidative Coupling Reactions Photocatalyzed by Zwitterionic Ligand Capped CsPbBr3Perovskite Quantum Dots

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 50, Pages 22563-22569

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007520

Keywords

C-C coupling; CsPbBr3; perovskite QDs; photocatalysis; stereoselectivity

Funding

  1. Brown University startup funds
  2. National Science Foundation [CBET-1936223, DMR-1943930]

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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 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 stereoselectivedl-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.

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