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2022 , Vol. 42 >Issue 1: 129 - 146

DOI: https://doi.org/10.6023/cjoc202107032

综述与进展

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
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  • 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

  网络出版日期: 2021-09-03

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)

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Progress in Selective Construction of Functional Aromatics with Cyclohexanone

  • Shuowen Wang ,
  • Pingyu Jiang ,
  • Rong Li ,
  • Muyang Yang ,
  • Guojun Deng
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  • College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105
* Corresponding author. E-mail:

Received date: 2021-07-15

  Revised date: 2021-08-15

  Online published: 2021-09-03

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)

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摘要

环己酮是一类廉价易得的重要的有机化工原料, 含有极性的活泼羰基, 可与亲核试剂进行亲核加成并进一步转化. 此外, 因羰基的活化作用, 其邻位的亚甲基也具有较好的反应活性. 因而, 环己酮可以作为廉价的C2源参与成环及芳构化反应构筑芳香功能分子. 将从环己酮参与的选择性构建单取代芳烃、多取代芳烃以及杂环芳烃三个方面进行阐述, 重点综述近几年环己酮与醛、酮、胺、硫酚等亲核试剂经缩合、脱氢芳构化选择性构建功能芳烃的研究进展, 并对未来进一步开发新型温和绿色的合成方法实现环己酮选择性构建功能芳烃进行了展望.

关键词： 环己酮; 亲核加成; 脱氢芳构化; 缩合; 功能芳烃

本文引用格式

王硕文 , 姜平宇 , 李镕 , 杨沐阳 , 邓国军 . 环己酮选择性构建功能芳烃的研究进展[J]. 有机化学, 2022 , 42(1) : 129 -146 . DOI: 10.6023/cjoc202107032

Abstract

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

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