Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site

doi:10.6023/cjoc201903003

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1688-1694.DOI: 10.6023/cjoc201903003 Previous Articles Next Articles

Special Issue: 金属有机化学；碳氢活化合辑2018-2019

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氯化镍催化的过硫酸钠对芳烃苄位的氧化反应

刘立策^a, 吴杰庆^a, 马鸿飞^a, 张晗^b, 顾洁凡^a, 李玉峰^a

a 南京工业大学化学与分子工程学院南京 210036;
b 南京联科化学有限公司南京 210009

收稿日期:2019-03-02 修回日期:2019-04-18 发布日期:2019-04-26
通讯作者: 李玉峰 E-mail:yufengli@njtech.edu.cn

Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site

Liu Lice^a, Wu Jieqing^a, Ma Hongfei^a, Zhang Han^b, Gu Jiefan^a, Li Yufeng^a

a College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 210036;
b Nanjing UNOCI Chemical Co., Nanjing 210009

Received:2019-03-02 Revised:2019-04-18 Published:2019-04-26
Contact: 10.6023/cjoc201903003 E-mail:yufengli@njtech.edu.cn

1. Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site.PDF(1330KB)

Abstract

A practical method for the oxidation of aromatic side chains was established for the preparation of aromatic aldehydes and ketones. Using NiCl₂ as the catalyst, substituted toluenes were oxidized with Na₂S₂O₈ at the benzylic site for the synthesis of the corresponding aldehydes in the yield of 22%~79%. Ethylbenzene analogs were oxidized more easily to obtain the corresponding ketones with 64%~84% yields. The oxidation of benzyl alcohol analogs was completed to acquire the corresponding carbonyl compounds in shorter time with better selectivity and yields. The method has the advantages such as the mild reaction conditions, no requirement for precious metals or additional promoter, and good selectivity.

Key words: oxidation, aromatic hydrocarbon, benzyl alcohol, nickel chloride, sodium persulfate

Cite this article

Liu Lice, Wu Jieqing, Ma Hongfei, Zhang Han, Gu Jiefan, Li Yufeng. Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site[J]. Chin. J. Org. Chem., 2019, 39(6): 1688-1694.

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氯化镍催化的过硫酸钠对芳烃苄位的氧化反应

Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site

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