Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid

doi:10.6023/cjoc201212006

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 988-994.DOI: 10.6023/cjoc201212006 Previous Articles Next Articles

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环状磷酸催化合成二吲哚甲烷衍生物

何林^a, 王湘波^a, 杜广芬^a, 代斌^a, 简腾跃^b

a 石河子大学化学化工学院新疆兵团化工绿色过程重点实验室-省部共建国家重点实验室培育基地石河子 832000;
b 中国科学院化学研究所北京分子科学国家实验室中国科学院分子识别与功能重点实验室 100190

收稿日期:2012-12-06 修回日期:2013-01-27 发布日期:2013-02-05
通讯作者: 何林,helin@shzu.edu.cn E-mail:helin@shzu.edu.cn
基金资助:
石河子大学团队创新(No. 2011ZRKETD-0403)、中国科学院分子识别与功能重点实验室2009年开放基金(No. 2009LMRF002)资助项目.

Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid

He Lin^a, Wang Xiangbo^a, Du Guangfen^a, Dai Bin^a, Jian Tengyue^b

a Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan and School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832000;
b National Laboratory for Molecular Sciences, Chinese Academy of Sciences Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Received:2012-12-06 Revised:2013-01-27 Published:2013-02-05
Supported by:
Project supported by the Team Innovation Project of Shihezi University (No. 2011ZRKETD-0403), the Key Laboratory of Molecular Recognition and Function, Chinese Academy of Sciences (No. 2009LMRF002).

Cyclic phosphoric acid was found to be an efficient Brønsted acid catalyst for the electrophilic substitution reaction of indole with aldehydes or ketones in dichloromethane to afford the corresponding bis(indolyl)methanes in excellent yields at room temperature. The influence of catalyst structure, catalyst loading and reaction media was investigated, the optimal reaction conditions were obtained and a possible mechanism for the reaction was proposed. The simple procedure, mild reaction conditions, low catalyst loading, high yield and environmentally friendly organocatalyst provide a valuable approach for the preparation of bis(indolyl)methanes.

Key words: indole, aldehyde, ketone, cyclic phosphoric acid, bis(indolyl)methanes

Cite this article

He Lin, Wang Xiangbo, Du Guangfen, Dai Bin, Jian Tengyue. Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid[J]. Chin. J. Org. Chem., 2013, 33(05): 988-994.

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环状磷酸催化合成二吲哚甲烷衍生物

Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid

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