Citation: Yang Jinchuang, Li Guosong, Lü Chengwei, An Yue, Gao Shuang. Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex[J]. Chinese Journal of Organic Chemistry, ;2018, 38(11): 3070-3077. doi: 10.6023/cjoc201805034 shu

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

Yang Jinchuang ^a,b ,
Li Guosong ^b ,
Lü Chengwei ^a ,
An Yue ^a,, ,
Gao Shuang ^b,,

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

Corresponding author: An Yue, anyue_11@163.com Gao Shuang, sgao@dicp.ac.cn
Received Date: 16 May 2018
Revised Date: 19 June 2018
Available Online: 5 November 2018
Fund Project: the National Natural Science Foundation of China 21403100the Education Research Program of the Education Department of Liaoning Province L2014421Project 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)

Figures(2)

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.
- ligand N₄,
- manganese,
- oxidative kinetic resolution,
- aromatic sulfoxides,
- sulfone
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