Ionic Organic Solid 1,3-Bis(sulfomethyl)imidazoliumate as an Effective Metal-Free Catalyst for Sustainable Organic Syntheses.

Abstract

The 1,3-bis(sulfomethyl)imidazole (bsmim) was effectively prepared by a multicomponent reaction, employing aminomethanesulfonic acid, glyoxal, and formaldehyde. The catalytic activity of bsmim was tested in the synthesis of quinoline derivatives, by means of the Friedländer reaction, and in the allylic substitution of alcohols with nitrogen-containing heterocycles. The performance of sulfo-imidazole derivative (bsmim) resulted in higher comparison with the carboxyimidazole analogs (bcmim and bcmimCl), under the same reaction conditions. This type of ionic organic solid allows the promotion of reactions in the absence of solvent and mild reaction conditions, which improves the sustainability of organic synthetic processes.