Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 129-146.DOI: 10.6023/cjoc202107032 Previous Articles     Next Articles

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环己酮选择性构建功能芳烃的研究进展

王硕文, 姜平宇, 李镕, 杨沐阳, 邓国军*()   

  1. 湘潭大学化学学院 湖南湘潭 411105
  • 收稿日期:2021-07-15 修回日期:2021-08-15 发布日期:2021-09-02
  • 通讯作者: 邓国军
  • 基金资助:
    国家自然科学基金(21871226); 国家自然科学基金(21372187); 湖南省研究生科研创新(XDCX2021B151)

Progress in Selective Construction of Functional Aromatics with Cyclohexanone

Shuowen Wang, Pingyu Jiang, Rong Li, Muyang Yang, Guojun Deng()   

  1. College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105
  • Received:2021-07-15 Revised:2021-08-15 Published:2021-09-02
  • Contact: Guojun Deng
  • Supported by:
    National Natural Science Foundation of China(21871226); National Natural Science Foundation of China(21372187); Postgraduate Scientific Research Innovation Project of Hunan Province(XDCX2021B151)

Cyclohexanone, a cheap and important organic chemical material with polar active carbonyl group, can construct many functional materials via nucleophilic addition with nucleophiles and subsequent transformation. In addition, the methylene group in the ortho-position of carbonyl group also exhibits good reactivity. Therefore, cyclohexanone can be used as a versatile C2 source for cycloaddition reaction providing various aromatic compounds via subsequent dehydroaro- matization. The cyclohexanone involved reactions to chemoselectively produce monosubstituted aromatics, polysubstituted aromatics and heterocyclic aromatics is discussed. The addition reactions and further dehydroaromatization of cyclohexanone with nucleophiles such aldehydes, ketones, aromatic amines, thiophenols and unsaturated hydrocarbons are discussed in detail as well. The environmentally benign synthesis of aromatic functional molecules with cyclohexanone is prospected at the end of this review.

Key words: cyclohexanone, nucleophilic addition, dehydroaromatization, condensation, functional aromatics