Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4476-4483.DOI: 10.6023/cjoc202106017 Previous Articles     Next Articles

ARTICLES

三价铑催化通过环己二酮高效构建异香豆素类化合物

戴雨倩, 李兴伟, 刘丙贤*()   

  1. 河南师范大学化学化工学院 国家药监局创新药物研究与评价重点实验室 河南省精细化工绿色生产协同创新中心 河南新乡 453007
  • 收稿日期:2021-06-08 修回日期:2021-07-13 发布日期:2021-07-26
  • 通讯作者: 刘丙贤
  • 基金资助:
    国家自然科学基金(21801066); 国家自然科学基金(21525208); 国家自然科学基金(U1804283); 国家自然科学基金(21801067); 国家博士后科学基金(2020M682307); 国家博士后科学基金(2021T140183)

Rh(III)-Catalyzed Efficient Synthesis of Isocoumarins from Cyclohexanediones

Yuqian Dai, Xingwei Li, Bingxian Liu()   

  1. NMPA Key Laboratory for Research and Evaluation of Innovative Drug, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
  • Received:2021-06-08 Revised:2021-07-13 Published:2021-07-26
  • Contact: Bingxian Liu
  • Supported by:
    National Natural Science Foundation of China(21801066); National Natural Science Foundation of China(21525208); National Natural Science Foundation of China(U1804283); National Natural Science Foundation of China(21801067); China Postdoctoral Science Foundation(2020M682307); China Postdoctoral Science Foundation(2021T140183)

Isocoumarin skeleton is a kind of important motif of natural product and bio-active molecular. The synthesis of simple and efficient construction of isocoumarin is of great significance. This work realized the one-pot synthesis of cyclohexanone-isocoumarins by rohdium catalyzed aryl C—H activation and followed annulation with in-situ generated iodonium ylides of cyclohexanones. Divers directing groups can be tolerated under the system leading to the desired products, among which sulfoxonium ylides and benzoic acids exhibited good reaction efficiency. Control experiments, deuterium labeling experiments and isolation of the possible intermediate revealed that the in-situ generated iodonium ylides were necessary for the reaction system.

Key words: isocoumarins, iodonium ylides, C—H activation, Rh-catalysis