Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4690-4695.DOI: 10.6023/cjoc202106041 Previous Articles     Next Articles



代鹏程, 徐亮*()   

  1. 石河子大学化学化工学院 新疆兵团化工绿色过程重点实验室 新疆石河子 832003
  • 收稿日期:2021-06-23 修回日期:2021-08-02 发布日期:2021-08-17
  • 通讯作者: 徐亮
  • 基金资助:

Visible-Light-Induced Benzylic C—H Oxygenation Reaction Using Tetrabutylammonium Tribromide as the Catalyst

Pengcheng Dai, Liang Xu()   

  1. Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003
  • Received:2021-06-23 Revised:2021-08-02 Published:2021-08-17
  • Contact: Liang Xu
  • Supported by:
    National Natural Science Foundation of China(21963010)

The direct oxidative functionalization of the benzylic C—H bonds of alkyl arenes paves a way for the quick synthesis of carbonyl compounds, which is of great significance in organic synthesis. In the past decades, the photooxidative pathways to achieve this reaction have developed rapidly, using relatively green and readily available oxygen as the terminal oxidant under light irradiation. In this paper, a commercially available and inexpensive chemical reagent, tetrabutylammonium tribromide (TBATB), was used to catalyze the photooxidation of the benzylic C—H bonds. Under visible light irradiation and air atmosphere, a catalytic amount of TBATB was utilized to achieve the efficient conversion of alkyl arenes to the corresponding aryl ketones. The reaction is feasible under mild conditions and without any additives, leading to a broad scope of ketone substrates. This method can be an effective supplement to the current benzylic photooxidation reaction systems.

Key words: oxygenation reaction, visible-light photocatalysis, alkyl arenes, tetrabutylammonium tribromide