Brønsted Acid-Catalyzed Substitution Reactions of 2-Indolyl-methanols with Tryptophols: Chemoselective Synthesis of 2,2'-Bisindolylmethanes

doi:10.6023/cjoc202005096

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3895-3907.DOI: 10.6023/cjoc202005096 Previous Articles Next Articles

Special Issue: 创刊四十周年专辑

布朗斯特酸催化下2-吲哚甲醇与色醇的取代反应:2,2'-双吲哚甲烷的化学选择性合成

毛雨佳^a, 陆一楠^a, 李天真^a, 吴琼^b, 谭伟^a, 石枫^a

a 江苏师范大学化学与材料科学学院江苏徐州 221116;
b 徐州工程学院材料与化学工程学院江苏徐州 221018

收稿日期:2020-05-31 修回日期:2020-06-20 发布日期:2020-07-01
通讯作者: 石枫谭伟, 吴琼 E-mail:fshi@jsnu.edu.cn;wtan@jsnu.edu.cn;hgwuqiong@xzit.edu.cn
基金资助:
国家自然科学基金（Nos.21772069，21831007）、江苏省六大人才高峰（No.SWYY-025）、江苏高校品牌专业建设工程和大学生创新计划、江苏省高等学校自然科学研究面上（No.18KJB150031）资助项目.

Brønsted Acid-Catalyzed Substitution Reactions of 2-Indolyl-methanols with Tryptophols: Chemoselective Synthesis of 2,2'-Bisindolylmethanes

Mao Yujia^a, Lu Yinan^a, Li Tianzhen^a, Wu Qiong^b, Tan Wei^a, Shi Feng^a

a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116;
b School of Materials and Chemical Engineering, Xuzhou University of Technology, Xuzhou, Jiangsu 221018

Received:2020-05-31 Revised:2020-06-20 Published:2020-07-01
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772069, 21831007), the Six Kinds of Talents Project of Jiangsu Province (No. SWYY-025), Top-notch Academic Programs Project of Jiangsu Higher Education Institutions, the Undergraduate Students Innovative Project and the High Education Natural Science Foundation of Jiangsu Province (No. 18KJB150031).

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Abstract

A Brønsted acid-catalyzed substitution reaction of 2-indolylmethanols with tryptophols has been established, which afforded a series of 2,2'-bisindolylmethanes in high yields (up to 98% yield) with chemoselectivity. This protocol not only provides an efficient method for constructing biologically important 2,2'-bisindolylmethane frameworks, but also has realized a substitution reaction of 2-indolylmethanols, which will enrich the chemical property of 2-indolylmethanols. Moreover, this approach has utilized the C(2)-nucleophilicity of tryptophols, which provided a good example for controlling the chemoselectivity in tryptophol-involved reactions.

Key words: 2-indolylmethanol, tryptophol, Brønsted acid catalysis, substitution, bisindolylmethane

Cite this article

Mao Yujia, Lu Yinan, Li Tianzhen, Wu Qiong, Tan Wei, Shi Feng. Brønsted Acid-Catalyzed Substitution Reactions of 2-Indolyl-methanols with Tryptophols: Chemoselective Synthesis of 2,2'-Bisindolylmethanes[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3895-3907.

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布朗斯特酸催化下2-吲哚甲醇与色醇的取代反应:2,2'-双吲哚甲烷的化学选择性合成

Brønsted Acid-Catalyzed Substitution Reactions of 2-Indolyl-methanols with Tryptophols: Chemoselective Synthesis of 2,2'-Bisindolylmethanes

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