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


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-? interaction.

SUBMITTER: Wang X 

PROVIDER: S-EPMC6483367 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Wang Xu X   Aldrich Courtney C CC  

PloS one 20190425 4


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. ...[more]

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