| In this dissertation, the synthesis of a wide variety of carbo- and heterocycles has been achieved via palladium-catalyzed annulation of vinylic cyclopropanes, vinylic cyclobutanes, 1,4-dienes and internal alkynes.; The first part of the thesis discusses the palladium-catalyzed intermolecular arylation of functionally-substituted cyclic alkenes. The regioselectivity of the products significantly depends on the base employed in the reaction and the functional groups present on the cyclic olefin.; The second part discusses the synthesis of benzofuran, indole, and tetrahydroquinoline derivatives via palladium-catalyzed annulation of vinylic cyclopropanes, vinylic cyclobutanes and 1,4-dienes. Ortho-functionalized aryl iodides react with these alkenes in the presence of palladium acetate and an appropriate base to afford carbo- and heterocycles with good regioselectivity.; The third part of this thesis discusses the synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes. The annulation process provides a convenient entry into variously substituted indoles.; The fourth part discusses other examples of the palladium-catalyzed annulation of internal alkynes. The annulation provides disubstituted indene, benzopyran, isoquinoline, and isocoumarin derivatives regioselectively.; In conclusion, the palladium-catalyzed annulation of alkenes and alkynes provides a convenient, new route to the synthesis of a wide variety of carbo- and heterocycles. The process also exhibits high regioselectivity, proceeds under mild reaction conditions in high yields, and accommodates a wide variety of functionality. |
