Cu(OTf)2 and N-Sulfinylprolinamide Catalyzed Friedel-Crafts Reaction of Indoles with N-Sulfonylaldimines

doi:10.6023/cjoc201601025

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (6): 1351-1358.DOI: 10.6023/cjoc201601025 Previous Articles Next Articles

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Cu(OTf)₂和脯氨亚磺酰胺共同催化吲哚与N-磺酰醛亚胺的Friedel-Crafts反应

刘海华, 张东华, 王夏辉, 孟卫东, 黄焰根

东华大学化学化工与生物工程学院上海 201620

收稿日期:2016-01-20 修回日期:2016-02-15 发布日期:2016-02-24
通讯作者: 黄焰根 E-mail:hyg@dhu.edu.cn
基金资助:
上海市教委科研创新(No.13ZZ047)和中央高校基本科研业务费专项资金(No.2232015D3-13)资助项目.

Cu(OTf)₂ and N-Sulfinylprolinamide Catalyzed Friedel-Crafts Reaction of Indoles with N-Sulfonylaldimines

Liu Haihua, Zhang Donghua, Wang Xiahui, Meng Weidong, Huang Yangen

College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620

Received:2016-01-20 Revised:2016-02-15 Published:2016-02-24
Supported by:
Project supported by the Innovation Program of Shanghai Municipal Education Commission (No. 13ZZ047) and the Fundamental Research Funds for the Central Universities (No. 2232015D3-13).

1. Cu(OTf)₂ and N-Sulfinylprolinamide Catalyzed Friedel-Crafts Reaction of Indoles with N-Sulfonylaldimines.PDF(1108KB)

Abstract

3-Indolyl methanamine derivatives have attracted much attention due to their multiple potent bioactivities. The Friedel-Crafts reaction between indole and N-sulfonylaldimine is a major method for preparation of 3-indolyl methanamine derivatives, however, abundant bisindolyl methane will be formed during the reaction. 3-Indolylmethanamine derivatives were selectively synthesized in 65%~93% yields by the Friedel-Crafts amidoalkylation reaction of indoles and N-sulfonylaldimines utilizing Cu(OTf)₂ and N-sulfinylprolinamide as catalysts. This method exhibited several features such as broad substrate applicability, mild reaction condition and simple operation.

Key words: electrophilic substitution, heterocycles, N-sulfinylprolinamide, 3-indolyl methanamine derivatives, the Friedel- Crafts amidoalkylation

Cite this article

Liu Haihua, Zhang Donghua, Wang Xiahui, Meng Weidong, Huang Yangen. Cu(OTf)₂ and N-Sulfinylprolinamide Catalyzed Friedel-Crafts Reaction of Indoles with N-Sulfonylaldimines[J]. Chin. J. Org. Chem., 2016, 36(6): 1351-1358.

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Cu(OTf)₂和脯氨亚磺酰胺共同催化吲哚与N-磺酰醛亚胺的Friedel-Crafts反应

Cu(OTf)₂ and N-Sulfinylprolinamide Catalyzed Friedel-Crafts Reaction of Indoles with N-Sulfonylaldimines

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Cu(OTf)2和脯氨亚磺酰胺共同催化吲哚与N-磺酰醛亚胺的Friedel-Crafts反应