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Issue 2, 2012
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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

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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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Publication details

The article was received on 28 Jun 2011, accepted on 27 Sep 2011 and first published on 04 Nov 2011


Article type: Paper
DOI: 10.1039/C1OB06043K
Citation: 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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