Metal-Catalyzed Functionalization of C-C Bonds in Four-Membered Rings

The means to promote catalytic C-C bond-functionalization has gained a considerable attention in recent years and probably can be considered done of the most challenging and vibrant subjects in organometallic chemistry. This PhD thesis deals with the design of new metal-catalyzed functionalization of C-C bonds in four-membered ring frameworks. Specifically, we have demonstrated the viability of preparing γ-arylated ketones via Pd-catalyzed cleavage of C-C bonds in tert-cyclobutanol using aryl chloride or tosylate counterparts. We also successfully extended the scope of the metal-catalyzed C-C bond-cleavage of tert-cyclobutanols by using halo acetylene counterparts giving γ-alkynylated ketones. Subsequently, we further extended the interest for C-C bond-cleavage beyond the use of tert-cyclobutanols by developing a Ni-catalyzed C-C bond-cleavage event in benzocyclobutenones for preparing eight-membered rings via formal [4+4]-cycloaddition with dienes.