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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 1: 223 - 231

DOI: https://doi.org/10.6023/cjoc201808009

Articles

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

  • Yu Jiajia ,
  • Yang Shan ,
  • Wu Zhen ,
  • Zhu Chen
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  • 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 date: 2018-08-10

  Revised date: 2018-09-10

  Online published: 2018-10-12

Supported by

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

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Abstract

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

Cite this article

Yu Jiajia , Yang Shan , Wu Zhen , Zhu Chen . Annulation of Benzylic Alcohols with Alkynes for Rapid and Efficient Synthesis of Indenes and Spiroindenes[J]. Chinese Journal of Organic Chemistry, 2019 , 39(1) : 223 -231 . DOI: 10.6023/cjoc201808009

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