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

doi:10.6023/cjoc201808009

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

Articles

通过苄醇与炔烃的环化反应快速高效构建茚及螺环茚

余佳佳^a, 杨珊^a, 吴镇^a, 朱晨^a,b

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 E-mail:chzhu@suda.edu.cn
基金资助:
国家自然科学基金（No.21722205）资助项目.

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

Yu Jiajia^a, Yang Shan^a, Wu Zhen^a, Zhu Chen^a,b

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 E-mail:chzhu@suda.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21722205).

1. Annulation of Benzylic Alcohols with Alkynes for Rapid and Efficient Synthesis of Indenes and Spiroindenes.PDF(1942KB)

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

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Yu Jiajia, Yang Shan, Wu Zhen, Zhu Chen. Annulation of Benzylic Alcohols with Alkynes for Rapid and Efficient Synthesis of Indenes and Spiroindenes[J]. Chin. J. Org. Chem., 2019, 39(1): 223-231.

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通过苄醇与炔烃的环化反应快速高效构建茚及螺环茚

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

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