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The field of metal-catalyzed C H bond functionalizations is an incredibly vibrant and spans beyond the formations of biaryl motifs. The mechanistic aspects of the C H bond functionalization with metal-carboxylate complexes are highlighted. The role of additives, such as pivalic acid, is demonstrated with poorly reactive substrates. A chapter describes experimental and computational studies which suggested that a single pathway might be involved in the palladium-catalyzed C H bond functionalization of a wide range of (hetero)arenes. Afterward a general set of conditions are developed to form biaryls by direct arylation with a wide range of heteroarenes of various complexity level. The development of two new Pd-catalyzed methods based on our knowledge on the C H bond cleavage are apply to the formation of new scaffolds. Efforts toward the development of ligands to specifically promoted C H bond cleavage are presented. Lastly, most recent results on the study of the mechanism of theC H bond cleavage combining experimental and computational studies are discussed. In the second part of the thesis are presented our strategy toward the synthesis of ginkgolide C using gold catalysis.