Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5278515 | Tetrahedron Letters | 2009 | 4 Pages |
Abstract
We have developed an efficient organocatalyzed, multicomponent synthesis of diarylmethane derivatives from tertiary aromatic amines, formaldehyde and 2-naphthols via Mannich type Friedel-Crafts reaction. Several organocatalysts such as (â)-chinchonidine, l-proline, l-thiaproline, and l-pipecolonic acid have been screened for the reaction but the best results were obtained with l-proline. In this Mannich type Friedel-Crafts alkylation, tertiary aromatic amines react with formaldehyde-proline adduct to generate 1-(4-(dimethylamino)benzyl)pyrrolidinium-2-carboxylate intermediate, which undergoes nucleophilic addition to give substituted diarylmethanes in excellent yields.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Atul Kumar, Mukesh Kumar, Maneesh Kumar Gupta,