1H-Imidazole-1-Methanol and the Progress on the Synthesis of a New Asymmetric Flexible Tridentate Pincer Ligand Featuring a Rigid Backbone

Abstract

Imidazole structures have occupied a unique position in heterocyclic chemistry as a synthetic precursor to imidazole salts ultimately for the formation of N-heterocyclic carbenes (NHCs). Nitrogen heterocyclic carbenes (NHC) were first established by Skell in the 1950s and have been additionally developed by Fischer and his students who introduced carbenes into organic and inorganic chemistry in 1964. NHCs have been proven to be excellent ligands in metal-based catalysis. The first step in the synthesis was creating 1H-imidazole-1-methanol. This compound comprises an imidazole ring with a methanol group attached at 1-position affording an imine nitrogen able to receive a hydrogen bond and an alcohol able to donate to a hydrogen bond. The crystal structure of the alcohol precursor has been submitted for publication in the peer reviewed journal Acta Cryst E and has been since published. After a successful synthesis of 1H-imidazole-1-methanol, 1-(chloromethyl)-1H-imidazole has been obtained. Current progress toward the current synthesis of 1H-imidazole-1-methanamine will be presented.