Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

Thanigaimalai Pillaiyar; Masoud Sedaghati; Andhika B. Mahardhika; Lukas L. Wendt; Christa E. Müller

doi:10.3762/bjoc.17.102

Beilstein Journal of Organic Chemistry (Jun 2021)

Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

Thanigaimalai Pillaiyar,
Masoud Sedaghati,
Andhika B. Mahardhika,
Lukas L. Wendt,
Christa E. Müller

Affiliations

Thanigaimalai Pillaiyar: PharmaCenter Bonn, Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany, phone: +49-228-73-2301; Fax: +49-228-73-2567
Masoud Sedaghati: PharmaCenter Bonn, Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany, phone: +49-228-73-2301; Fax: +49-228-73-2567
Andhika B. Mahardhika: PharmaCenter Bonn, Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany, phone: +49-228-73-2301; Fax: +49-228-73-2567
Lukas L. Wendt: PharmaCenter Bonn, Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany, phone: +49-228-73-2301; Fax: +49-228-73-2567
Christa E. Müller: PharmaCenter Bonn, Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany, phone: +49-228-73-2301; Fax: +49-228-73-2567

DOI: https://doi.org/10.3762/bjoc.17.102
Journal volume & issue: Vol. 17, no. 1
pp. 1464 – 1475

Abstract

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A novel, versatile approach for the synthesis of unsymmetrical 3,3'-diindolylmethanes (DIMs) with a quaternary carbon center has been developed via iodine-catalyzed coupling of trifluoromethyl(indolyl)phenylmethanols with indoles. In contrast to previously reported methods, the new procedure is characterized by chemoselectivity, mild conditions, high yields, and scalability to obtain gram amounts for biological studies. Selected compounds were found to display affinity for cannabinoid receptors, which are promising drug targets for the treatment of inflammatory and neurodegenerative diseases.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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