Citation: 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. doi: 10.6023/cjoc202005096 shu

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

Corresponding author: Wu Qiong, hgwuqiong@xzit.edu.cn Tan Wei, wtan@jsnu.edu.cn Shi Feng, fshi@jsnu.edu.cn

^†

Received Date: 31 May 2020
Revised Date: 20 June 2020
Available Online: 30 June 2020
Fund Project: the National Natural Science Foundation of China 21831007the Undergraduate Students Innovative Project and the High Education Natural Science Foundation of Jiangsu Province 18KJB150031the National Natural Science Foundation of China 21772069the Six Kinds of Talents Project of Jiangsu Province SWYY-025Project 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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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.
- 2-indolylmethanol,
- tryptophol,
- Brønsted acid catalysis,
- substitution,
- bisindolylmethane
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