Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 3070-3077.DOI: 10.6023/cjoc201805034 Previous Articles     Next Articles



杨金闯a,b, 李国松b, 吕成伟a, 安悦a, 高爽b   

  1. a 辽宁师范大学化学化工学院 大连 116029;
    b 中国科学院大连化学物理研究所国家清洁能源实验室 大连 116023
  • 收稿日期:2018-05-16 修回日期:2018-06-19 发布日期:2018-07-05
  • 通讯作者: 安悦, 高爽;
  • 基金资助:


Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex

Yang Jinchuanga,b, Li Guosongb, Lü Chengweia, An Yuea, Gao Shuangb   

  1. a Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023;
    b College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029
  • Received:2018-05-16 Revised:2018-06-19 Published:2018-07-05
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21403100) and the Education Research Program of the Education Department of Liaoning Province (No. L2014421).

Oxidative kinetics resolution of racemic aromatic sulfoxide was studied by using chiral porphyrin-inspired N4 ligands and manganese in situ complex as catalyst, environment-friendly H2O2 as oxidant and adamantanecarboxylic acid as additive. The arylalkyl and arylbenzyl sulfoxide substrates were extended by this catalytic system. A maximum yield of chiral sulfoxide was 40% and the enantioselectivity was 100%. In the meantime, the yield of sulfone a further oxidation products of sulfoxide, was up to 72%. It was found that the catalytic oxidation system is more prone to electron-rich sulfoxide through the competition experiment between electron-rich sulfoxide and electron-deficient sulfoxide substrates. In addition, the success of gram-scale oxidation kinetic resolution also shows that this method has a certain practical value in methodology.

Key words: ligand N4, manganese, oxidative kinetic resolution, aromatic sulfoxides, sulfone