有机化学 ›› 2021, Vol. 41 ›› Issue (11): 4306-4319.DOI: 10.6023/cjoc202105029 上一篇    下一篇

综述与进展

基于O-环己二烯酮型1,6-烯炔合成氢化苯并呋喃的反应研究进展

李志清b, 邱潇杨b, 孟楠b, 柳竹青a,b,*()   

  1. a 齐鲁工业大学前沿交叉学科研究院 济南 250353
    b 山东潍坊润丰化工股份有限公司 山东潍坊 250101
  • 收稿日期:2021-05-15 修回日期:2021-06-21 发布日期:2021-07-05
  • 通讯作者: 柳竹青
  • 基金资助:
    国家自然科学基金(22001140); 山东省自然科学基金(ZR2020QB002)

Progress in the Synthesis of Hydrobenzofurans from O-Cyclohexadienone-tethered 1,6-Enynes

Zhiqing Lib, Xiaoyang Qiub, Nan Mengb, Zhuqing Liua,b()   

  1. a Advanced Research Institute for Multidisciplinary Science, Qilu University of Technology, Jinan 250353
    b Shandong Weifang Rainbow Chemical Co. Ltd., Weifang, Shandong 250101
  • Received:2021-05-15 Revised:2021-06-21 Published:2021-07-05
  • Contact: Zhuqing Liu
  • Supported by:
    National Natural Science Foundation of China(22001140); Natural Science Foundation of Shandong Province(ZR2020QB002)

氢化苯并呋喃骨架广泛存在于生物活性分子、天然产物和药物分子中, 过渡金属催化的O-环己二烯酮型1,6-烯炔经分子内或分子间C—H键官能团化/环化串联反应是构建这类骨架较为经济、有效的方法. 总结了过渡金属催化O-环己二烯酮型1,6-烯炔经C—H键官能团化/环化串联反应合成氢化苯并呋喃类化合物反应的研究进展, 主要介绍了各类过渡金属催化的反应类型、反应机理和手性控制中配体的选择, 并对该领域所面临的挑战和发展前景进行了展望与探讨.

关键词: O-环己二烯酮型1,6-烯炔, 环化反应, C—H键官能团化, 氢化苯并呋喃

Hydrobenzofurans are abundant in bioactive molecules, natural products and drug molecules. Transition-metal- catalyzed intramolecular or intermolecular C—H bond functionalization/cyclization cascade of O-linkered cyclohexadienone-tethered 1,6-enynes is an economic and efficient way to construct this skeleton. The progress in the synthesis of hydrobenzofurans from cyclohexadienone-tethered 1,6-enynes via C—H bond functionalization/cyclization cascade catalyzed by different transition-metals is discussed. The relevant reaction modes, mechanisms and the selection of ligands for chiral control are mainly introduced. Finally, the challenges and development prospects in this field are also prospected and discussed.

Key words: O-cyclohexadienone-tethered 1,6-enyne, cyclization reaction, C—H bond functionalization, hydrobenzofuran