Date of Award
Doctor of Philosophy
Richard C. Larock
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.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Eul Kgun Yum
Yum, Eul Kgun, "Synthesis of carbo- and heterocycles via palladium-catalyzed annulation of alkenes and alkynes " (1992). Retrospective Theses and Dissertations. 10752.