Organic & Biomolecular Chemistry 2012-01-14

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, Sudipta Raha Roy, Dinesh Kumar, Chetna Madaan, Santosh Rudrawar, Asit K Chakraborti

Index: Org. Biomol. Chem. 10(2) , 281-6, (2012)

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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.