Development of an imidazole salt catalytic system for the preparation of bis(indolyl) methanes and bis(naphthyl)methane

Xu Wang; Courtney C. Aldrich

doi:10.1371/journal.pone.0216008

Development of an imidazole salt catalytic system for the preparation of bis(indolyl) methanes and bis(naphthyl)methane

Xu Wang, Courtney C. Aldrich

Medicinal Chemistry

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8 Scopus citations

Abstract

Imidazolium salts are shown to catalyze the rapid room temperature reaction of indoles or naphthol with aldehydes to provide bis(indolyl)methanes or bis(naphthol)methane in excellent yields and the reaction proceeds optimally in dichloromethane with no base additives. The reaction exhibits a broad substrate tolerance and occurs through nucleophilic activation of the indoles and naphthols through a cation–π interaction.

Original language	English (US)
Article number	e0216008
Journal	PloS one
Volume	14
Issue number	4
DOIs	https://doi.org/10.1371/journal.pone.0216008
State	Published - Apr 2019

Bibliographical note

Funding Information:
This work was supported by the grant of The State Key Laboratory of Bioactive Substance and Function of Natural Medicines (SKLBSFNM) and by the Union Scholar Chair Professor in Institute Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College (PUMC) to C.C.A. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.

Publisher Copyright:
© 2019 Wang, Aldrich. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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abstract = "Imidazolium salts are shown to catalyze the rapid room temperature reaction of indoles or naphthol with aldehydes to provide bis(indolyl)methanes or bis(naphthol)methane in excellent yields and the reaction proceeds optimally in dichloromethane with no base additives. The reaction exhibits a broad substrate tolerance and occurs through nucleophilic activation of the indoles and naphthols through a cation–π interaction.",

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Development of an imidazole salt catalytic system for the preparation of bis(indolyl) methanes and bis(naphthyl)methane

Abstract

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