Thieme Chemistry Journal Awardees - Whereare They Now? Synthesis of Diamantane-Derived N-HeterocyclicCarbenes and Applications in Catalysis

Novel diamantyl-substituted imidazolium salts have been synthesized,characterized and, in addition, analyzed by single-crystal structuralanalysis. The corresponding NHCs ( A-IDAdand M-IDAd) have been prepared in solutionand have been characterized by NMR. They exhibit increased stericdemand and increased lipophilicity relative to the well-known IAd.In comparative studies, these NHCs were tested as ligands in palladium-catalyzedSonogashira reactions of primary alkyl halides and, in addition,as catalysts in an organocatalyzed silyl enol ether formation.