Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles: Synthesis of 1,1-Diarylethanes

doi:10.6023/cjoc201601002

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1014-1020.DOI: 10.6023/cjoc201601002 Previous Articles Next Articles

ARTICLE

布朗斯特酸催化下邻羟基苯乙烯与吲哚的反应——1,1-二芳基乙烷类化合物的合成

江晓莉, 戴伟, 赵佳佳, 石枫

江苏师范大学化学化工学院徐州 221116

收稿日期:2016-01-02 修回日期:2016-01-26 发布日期:2016-02-02
通讯作者: 石枫 E-mail:fshi@jsnu.edu.cn
基金资助:
国家自然科学基金(No.21372002)、江苏高校品牌专业建设工程资助项目.

Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles: Synthesis of 1,1-Diarylethanes

Jiang Xiaoli, Dai Wei, Zhao Jiajia, Shi Feng

School of Chemistry & Chemical Engineering, Jiangsu Normal University, Xuzhou 221116

Received:2016-01-02 Revised:2016-01-26 Published:2016-02-02
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372002) and the Brand Major of Universities in Jiangsu Province.

1. Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles: Synthesis of 1,1-Diarylethanes.PDF(1750KB)

Abstract

The skeleton of 1,1-diarylethane exists in many biologically important molecules. So, the synthesis of 1,1-diarylethanes has absorbed great attention from the chemists. This work has established a reaction of ortho-hydroxylstyrenes with indoles in the presence of racemic phosphoric acid, leading to the efficient synthesis of a series of 1,1-diarylethanes with structural diversity in high yields (up to 99%). This reaction is based on the fact that ortho-hydroxylstyrenes could transform into ortho-quinone methide under the catalysis of racemic phosphoric acid. The dual activation mode of racemic phosphoric acid to ortho-quinone methide and indole via forming two hydrogen bonds contributed greatly to the efficiency of the reaction. The mild reaction condition and wide substrate scope of the reaction will not only provide a useful strategy for solving the problems of residual metal and harsh reaction condition associated with metal catalysis, but also expand the applicability of organocatalytic reactions for the synthesis of 1,1-diarylethanes.

Key words: Brø, nsted acid catalysis, organocatalysis, 1,1-diarylethane, ortho-hydroxylstyrene, indole, ortho-quinone methide

Cite this article

Jiang Xiaoli, Dai Wei, Zhao Jiajia, Shi Feng. Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles: Synthesis of 1,1-Diarylethanes[J]. Chin. J. Org. Chem., 2016, 36(5): 1014-1020.

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布朗斯特酸催化下邻羟基苯乙烯与吲哚的反应——1,1-二芳基乙烷类化合物的合成

Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles: Synthesis of 1,1-Diarylethanes

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