Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 242-248.DOI: 10.6023/cjoc202106023 Previous Articles     Next Articles



王璐a, 邵莺a, 陈帆b, 钱鹏程b,*(), 成江a,b,*()   

  1. a 常州大学石油化工学院 江苏常州 213164
    b 温州大学化学与材料工程学院 浙江温州 325035
  • 收稿日期:2021-06-10 修回日期:2021-07-14 发布日期:2021-09-02
  • 通讯作者: 钱鹏程, 成江
  • 基金资助:
    国家自然科学基金(21971025); 先进催化与绿色制造协同创新中心资助项目; 江苏省先进催化材料与技术重点实验室(BM2012110); 温州市科技局基金(W20170003)

Rhodium-Catalyzed Directing Group-Assisted Annulation of Arene C—H Bond with Vinylene Carbonate toward Isocoumarins

Lu Wanga, Ying Shaoa, Fan Chenb, Pengcheng Qianb(), Jiang Chenga,b()   

  1. a School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
    b College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
  • Received:2021-06-10 Revised:2021-07-14 Published:2021-09-02
  • Contact: Pengcheng Qian, Jiang Cheng
  • Supported by:
    National Natural Science Foundation of China(21971025); Advanced Catalysis and Green Manufacturing Collaborative Innovation Center; “Innovation & Entrepreneurship Talents” Introduction Plan of Jiangsu Province, the Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology(BM2012110); Foundation of Wenzhou Science & Technology Bureau(W20170003)

Isocoumarins are an important pharmaceutical compounds. Many synthetic pathways have been developed, mainly focusing on the cyclization of benzoic acid or other with alkynes. Sulfinylidene benzamides were facilely prepared and developed in the chelation-assisted arene ortho-C—H functionalization, and vinylene carbonate can establish an oxidant-free catalytic system, giving carbonic acid as a sole side product. In the presence of rhodium catalyst, an annulation between sulfinylidene benzamides and vinylene carbonate was developed, proceeding with directing group-assisted ortho-C—H coupling and intramolecular alcoholysis toward nonsubstituted isocoumarins in moderate to good yields.

Key words: rhodium, sulfinylidene benzamides, vinylene carbonate