Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2715-2722.DOI: 10.6023/cjoc202101031 Previous Articles     Next Articles



王微, 崔雪, 马健婷, 李友宾*(), 王雪松*()   

  1. 海南医学院药学院 热带转化医学教育部重点实验室 海南省热带药用植物研究开发重点实验室 海口市黎族医药重点实验室 海口 571199
  • 收稿日期:2021-01-18 修回日期:2021-04-08 发布日期:2021-04-25
  • 通讯作者: 李友宾, 王雪松
  • 作者简介:
    † 共同第一作者(These authors contributed equally to this work).
  • 基金资助:
    海南省自然科学青年基金(820QN264); 2019年海南省基础与应用基础研究计划(自然科学领域)高层次人才基金(2019RC214); 海南医学院引进人才启动基金(XRC180009)

Base-Promoted Ring Expansion Reactions for the Construction of Cycloheptanones through C—C Bond Cleavage

Wei Wang, Xue Cui, Jianting Ma, Youbin Li(), Xuesong Wang()   

  1. Key Laboratory of Tropical Translational Medicine of Ministry of Education, Hainan Provincial Key Laboratory for Research and Development of Tropical Herbs, Haikou Key Laboratory of Li Nationality Medicine, School of Pharmacy, Hainan Medical University, Haikou 571199
  • Received:2021-01-18 Revised:2021-04-08 Published:2021-04-25
  • Contact: Youbin Li, Xuesong Wang
  • Supported by:
    Hainan Provincial Natural Science Youth Foundation of China(820QN264); High-level Talents Fund of Basic and Applied Basic Research Program (Natural Science) of Hainan Province in 2019(2019RC214); Talent Introduction Start-up Fund of Hainan Medical University(XRC180009)

An efficient ring expansion strategy has been developed for the construction of cycloheptanones through C—C bond cleavage. The reactions take place with easily accessible starting materials, good functional group tolerance, and mild reaction conditions in the presence of Cs2CO3 without any metal or oxidant reagent. The transition-metal free insertions of alkynes into carbon-carbon σ-bonds of acenaphthenone initialized through intramolecular nucleophilic addition/ring-opening to furnish multifarious cycloheptanones, which has the potential to be widely utilized in organic synthetic chemistry.

Key words: C—C bond cleavage, ring expansion, base-promoted, cycloheptanone compounds