Journal of Liaoning Petrochemical University

Journal of Liaoning Petrochemical University ›› 2018, Vol. 38 ›› Issue (05): 14-18.DOI: 10.3969/j.issn.1672-6952.2018.05.003

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Aza-Henry Reaction Induced by Photosensitizer under the Visible Light Conditions

Li Shijie1,Yan Fei2,Wang Jingyun1,Zhou Mingdong1   

  1. (1.College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun Liaoning 113001, China; 2.Liaoning Province Product Quality Supervision and Inspection Institute, Shenyang Liaoning 110032, China)
  • Received:2017-04-06 Revised:2018-06-05 Published:2018-10-26 Online:2018-11-02

可见光条件下光敏剂引发的Aza-Henry反应

李世杰1闫飞2王景芸1周明东1   

  1. (1.辽宁石油化工大学 化学化工与环境学部,辽宁 抚顺 113001;2.辽宁省产品质量监督检验院,辽宁 沈阳 110032)
  • 通讯作者: 周明东(1980-),女,博士,教授,从事分子催化与有机合成化学的研究;E-mail:mingdong.zhou@hotmail.com
  • 作者简介:李世杰(1991-),男,硕士研究生,从事有机光化学研究;E-mail:1195543639@qq.com
  • 基金资助:
    辽宁省自然科学基金项目(2015020196)

Abstract: 3-Methoxythioxanthone was synthesized, and the structure is identified by1H NMR, 13C NMR, IR and HRMS spectra. The UV-Vis absorption spectra of 3-Methoxythioxanthone shows that it absorbs near the purple light (380 nm) in the visible range and is a visible light photosensitizer. 3-Methoxythioxanthone was applied to the Aza-Henry reaction of 2-phenyl-1,2,3,4-Tetrahydroisoquinoline and Nitromethane. Under the irradiation of purple LED, the photosensitizer with a molar fraction of 5% allowed the reaction to be isolated in a yield of 84% within 6 h. According to the experimental results, the mechanism of photocatalytic reaction of AzaHenry was proposed. The photosensitizer could transfer energy to produce singlet oxygen under the illumination, and singlet oxygen promoted the Aza-Henry reaction.

Key words: Visible light, Photosensitizer, Aza-Henry reaction

摘要: 合成了3-甲氧基噻吨酮,并通过核磁共振、红外光谱、高分辨质谱对其结构进行表征。3-甲氧基噻吨酮紫外-可见光谱表明,其在可见光范围内的紫色光(380 nm)附近有吸收,是一种可见光光敏剂。将该光敏剂应用于2-苯基-1,2,3,4-四氢异喹啉和硝基甲烷的Aza-Henry反应中,在紫色LED光照射的条件下,摩尔分数为5%的光敏剂使反应在6 h内产物的分离产率为84%。根据实验结果,提出了光催化的Aza-Henry反应机理,光敏剂在光照条件下进行能量转移产生单线态氧,单线态氧促进Aza-Henry反应的进行。

关键词: 可见光, 光敏剂, Aza-Henry反应

Cite this article

Li Shijie,Yan Fei,Wang Jingyun,Zhou Mingdong. Aza-Henry Reaction Induced by Photosensitizer under the Visible Light Conditions[J]. Journal of Liaoning Petrochemical University, 2018, 38(05): 14-18.

李世杰,闫飞,王景芸,周明东. 可见光条件下光敏剂引发的Aza-Henry反应[J]. 辽宁石油化工大学学报, 2018, 38(05): 14-18.