Date : 2014. 5. 8, 4:30 PM Place : Int"l conf. room, Bldg.25-1 -Abstract- The C-H bond functionalization reaction allows for straightforward and efficient access to biologically important compounds and functional materials. Two different approaches based on the C-H bond functionalization will be discussed: the construction of new scaffolds by rhodium vinylidene catalysis and the direct C-H arylation of the existing heterocyclic cores by palladium carboxylate catalysis. In contrast to traditional alkynylation reactions, metal alkynyls can react with electrophiles through the β-carbon to provide metal vinylidene species. We developed a tandem catalytic process that integrates the β-alkylation of a metal alkynyl and subsequent turnover of the resulting metal vinylidene to furnish 5,6-fused ring systems. The synthetic utility of the metal vinylidene-mediated cyclization method has been demonstrated in the concise synthesis of an erythrina alkaloid, 3-demethoxyerythratidinone. Functionalized azoles and azines are important heterocycles, frequently found in pharmaceuticals, synthetic biological probes, and functional materials. We developed a general and comprehensive approach for the synthesis of complex aryl imidazoles and 1,2,4-triazoles, where all C-H bonds of the parent rings can be arylated in a regioselective and sequential manner. The electronic and steric effects of the heteroarene ring that led to the development of the regioselective C-;H arylation reaction of pyridines will also be discussed.