Issue 2, 2012
From the journal:

Organic & Biomolecular Chemistry

Lack of correlation between catalytic efficiency and basicity of amines during the reaction of aryl methyl ketones with DMF-DMA: an unprecedented supramolecular domino catalysis†

Anirban Sarkar,a   Sudipta Raha Roy,a   Dinesh Kumar,a   Chetna Madaan,a   Santosh Rudrawara  and  Asit K. Chakraborti*a  

* Corresponding authors

a Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab, India
E-mail: akchakraborti@niper.ac.in

Abstract

1-Methylimidazole exhibits an unusually high efficiency in promoting the reaction of aryl methyl ketones with DMF-DMA to form (2E)-1-aryl-3-dimethylamino-2-propenones which lacks correlation between the catalytic efficiency and the basicity of 1-methylimidazole in comparison to other amines. An unprecedented supramolecular domino catalysis rationalises the lack of correlation between the catalytic efficiency and basicity of the amines. The supramolecular assemblies have been characterized by mass-spectrometric ion fishing. The time-dependent increase/decrease in the concentration (ion current) of the supramolecular species consolidated the mechanism.

Graphical abstract: Lack of correlation between catalytic efficiency and basicity of amines during the reaction of aryl methyl ketones with DMF-DMA: an unprecedented supramolecular domino catalysis

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Article information

DOI
https://doi.org/10.1039/C1OB06043K
Article type
Paper
Submitted
28 Jun 2011
Accepted
27 Sep 2011
First published
04 Nov 2011

Org. Biomol. Chem., 2012,10, 281-286

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Lack of correlation between catalytic efficiency and basicity of amines during the reaction of aryl methyl ketones with DMF-DMA: an unprecedented supramolecular domino catalysis

A. Sarkar, S. Raha Roy, D. Kumar, C. Madaan, S. Rudrawar and A. K. Chakraborti, Org. Biomol. Chem., 2012, 10, 281 DOI: 10.1039/C1OB06043K

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