Issue 93, 2022
From the journal:

Chemical Communications

Oxidative two-way regiocontrolled coupling of 3-methoxycarbonylcatechol and indoles to arylindoles†

Yoshinari Sawama, ORCID logo *a   Shoko Kuwata,b   Miyu Mae,a   Taro Udagawa, ORCID logo c   Shuji Akai ORCID logo a  and  Hironao Sajiki ORCID logo b  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan
E-mail: sawama@phs.osaka-u.ac.jp

b A Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4-Daigaku-nishi, Gifu 501-1196, Japan

c Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan

Abstract

3-Methoxycarbonylcatechol effectively underwent two-way regiocontrolled coupling with indoles via an ortho-benzoquinone intermediate, resulting from phenyliodine(III) diacetate oxidation, to generate 4-adducts or 5-adducts with or without BF3·Et2O in a one-pot manner. DFT calculations confirmed the obtained regioselectivities.

Graphical abstract: Oxidative two-way regiocontrolled coupling of 3-methoxycarbonylcatechol and indoles to arylindoles

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Article information

DOI
https://doi.org/10.1039/D2CC04843D
Article type
Communication
Submitted
01 Sep 2022
Accepted
24 Oct 2022
First published
24 Oct 2022

Chem. Commun., 2022,58, 12935-12938

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Oxidative two-way regiocontrolled coupling of 3-methoxycarbonylcatechol and indoles to arylindoles

Y. Sawama, S. Kuwata, M. Mae, T. Udagawa, S. Akai and H. Sajiki, Chem. Commun., 2022, 58, 12935 DOI: 10.1039/D2CC04843D

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