Thieme Chemistry Journal Awardees - Where are They Now? Synthesis of Diamantane-Derived N-Heterocyclic Carbenes and Applications in Catalysis

Richter H, Schwertfeger H, Schreiner PR, Frohlich R, Glorius F

Abstract

Novel diamantyl-substituted imidazolium salts have been synthesized, characterized and, in addition, analyzed by single-crystal structural analysis. The corresponding NHCs (a-IDAd and m-IDAd) have been prepared in solution and have been characterized by NMR. They exhibit increased steric demand and increased lipophilicity relative to the well-known IAd. In comparative studies, these NHCs were tested as ligands in palladium-catalyzed Sonogashira reactions of primary alkyl halides and, in addition, as catalysts in an organocatalyzed silyl enol ether formation.