Yuan Yucheng, Zhu Hua, Hills-Kimball Katie, Cai Tong, Shi Wenwu, Wei Zichao, Yang Hanjun, Candler Yolanda, Wang Ping, He Jie, Chen Ou
Department of Chemistry, Brown University, 324 Brook St., Providence, RI, 02912, USA.
Department of Chemistry, University of Connecticut, 55 North Eagleville Rd., Storrs, CT, 06269, USA.
Angew Chem Int Ed Engl. 2020 Dec 7;59(50):22563-22569. doi: 10.1002/anie.202007520. Epub 2020 Oct 8.
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 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.
半导体量子点（QDs）因其在光催化反应中具有优异的光电性能，包括高吸收系数和长光生载流子寿命，在光催化领域引起了极大关注。在此，通过选择2-(3,4-二甲氧基苯基)-3-氧代丁腈作为模型底物，我们证明了在可见光照射下，使用两性离子配体封端的CsPbBr钙钛矿量子点可以实现立体选择性（>99%）的C-C氧化偶联反应，且产物收率高（99%）。该反应可以推广到苯环上具有各种取代基和不同官能团的不同起始原料，生成立体选择性的dl-异构体。我们提出了一种自由基介导的反应途径。我们的研究提供了一种通过使用特殊设计的钙钛矿量子点进行光催化手段实现立体选择性C-C氧化偶联的新方法。
