May 6, 2024
Dariush Saberi

Dariush Saberi

Academic Rank: Associate professor
Address:
Degree: Ph.D in Chemistry
Phone: 07731222424
Faculty: Faculty of Nano and Biotechnology

Research

Title N-Heterocyclic carbene-catalyzed condensation/oxidation/ cyclization/aromatization cascade for the synthesis of tri- and tetra-substituted imidazoles
Type Article
Keywords
Benzoin Condensation, Cascade reaction, N-Heterocyclic carbenes, Oxidation, tri(tetra)-Substituted imidazoles.
Journal Asian Journal of Organic Chemistry
DOI 10.1002/ajoc.202300001
Researchers Najmeh Nowrouzi (Second researcher) , Dariush Saberi (Third researcher)

Abstract

In this study, a novel and efficient onepot tandem synthesis of 2,4,5-tri- and 1,2,4,5-tetrasubstituted imidazoles is described. In the first step of the sequence, benzil is formed via benzoin condensation catalyzed by N-heterocyclic carbene, followed by in situ aerobic oxidation. Next, it is reacted with another aldehyde and ammonium acetate (or amine) to produce the polysubstituted imidazole. The reaction proceeds smoothly in high yield and short reaction time in ethanol as a green solvent. The current strategy shows high functional group tolerance with respect to aldehydes and avoids the need for ligands and reducing agents. This method allows the synthesis of complex molecules in a one-pot procedure without isolating intermediates.