Journal
TETRAHEDRON LETTERS
Volume 50, Issue 50, Pages 7024-7027Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.09.155
Keywords
Organocatalyst; Friedel-Crafts reaction; Diarylmethane derivatives; Multicomponent reaction
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Funding
- CSIR-UGC, New Delhi
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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 (-)-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. (C) 2009 Elsevier Ltd. All rights reserved.
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