Use of a Biomimetic Catalyst in the Benzoin Condensation

The traditional undergraduate organic laboratory “Benzoin condensation” is performed with the aid of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, a biomimetic catalyst modeled on vitamin B1. For comparison, the classical catalysts for this reaction, sodium cyanide and vitamin B1, are also used. The performance of the synthetic thiazolium catalyst is comparable, and in some terms superior, to cyanide and thiamin hydrochloride. The students are able to find suitable reaction conditions for each experiment, and draw conclusions about the differences and similarities between organic and biochemical reactions. The experiment serves to illustrate the transfer of knowledge between biochemistry and organic chemistry, which contributes to the advancement of both disciplines.