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This thesis presents the development of new catalysts for the palladium-catalyzed Ntert-prenylation of indoles, the rhodium-catalyzed endoand enantioselective hydroacylation of ortho-allylbenzaldehydes, studies toward the rhodium-catalyzed intramolecular hydroacylation of 1,2-disubstituted alkenes, and the first examples of the rhodium-catalyzed, enantioselective hydroacylation of 1,1,2-trisubstituted alkenes. Chapter II discusses the development of three distinct protocols for the synthesis of N-tert-prenylindoles using indole, (η-indole)Cr(CO)3, and indoline nucleophiles. These reactions occur in the presence of the same palladium catalyst prepared in situ from readily available precursors and require loadings of the palladium catalyst that are up to ten times less than required for previously reported direct N-tert-prenylations of indoles. These methods for palladium-catalyzed N-tert-prenylation generate N-tert-prenylindoles with a range of electronic character in high yields (up to 94%) with high tert-prenyl-to-n-prenyl selectivity (up to 12:1). Chapter III describes the development of a rhodium catalyst for endoand enantioselective hydroacylation of ortho-allylbenzaldehydes. A catalyst generated from [Rh(COD)Cl]2, (R)-DTBM-Segphos and NaBARF promotes the enantioselective hydroacylation reactions and minimizes the formation of byproducts from competitive alkene isomerization and ene/dehydration pathways. These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2H)-one products in moderate-to-high yields (49-91%) with excellent enantioselectivities (96-99% ee).

Transition metal-catalyzed C-N and C-C bond formation: N-tert-prenylation and alkene hydroacylation