Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 223-231.DOI: 10.6023/cjoc201808009 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞



余佳佳a, 杨珊a, 吴镇a, 朱晨a,b   

  1. a 苏州大学材料与化学化工学部 苏州 215123;
    b 中国科学院上海有机化学研究所 天然产物有机合成重点实验室 上海 200032
  • 收稿日期:2018-08-10 修回日期:2018-09-10 发布日期:2018-10-12
  • 通讯作者: 朱晨
  • 基金资助:


Annulation of Benzylic Alcohols with Alkynes for Rapid and Efficient Synthesis of Indenes and Spiroindenes

Yu Jiajiaa, Yang Shana, Wu Zhena, Zhu Chena,b   

  1. a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123;
    b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Shanghai 200032
  • Received:2018-08-10 Revised:2018-09-10 Published:2018-10-12
  • Contact: 10.6023/cjoc201808009
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21722205).

As a type of important carbocyclic compounds, indenes and spiroindenes are not only widely found in natural products but extensively employed as synthetic building blocks in materials, pharmaceuticals, and asymmetric synthesis. An efficient and rapid synthesis of indenes and spiroindenes via the annulation of benzylic alcohols (or aryl-substituted cycloalkanols) with alkynes in the presence of TiCl4 or AlCl3 was desclosed. This reaction is normally completed within 30 min at room temperature and compatible with a variety of substituted alkynes. Two new C—C bonds are constructed during the reaction. Cycloalkanols such as cyclobutanol, cyclohexanol, cycloheptanol, cyclooctanol, and cyclododecanol are suitable substrates to afford a set of valuable spiroindenes. This method is featured with simple operation, short reaction time, and mild reaction conditions.

Key words: Lewis acid, cyclization, indene, spiroindene