Catalytic Addition of Nucleophiles to Unactivated Olefins

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This project addresses the development of Pd(II)-, Pt(II)-, and Au(I)-catalyzed processes for the addition of C-, N-, and O-nucleophiles to unactivated olefins. The scope of the Pt-catalyzed alkylation of indoles will be explored, and an effective protocol for the asymmetric cyclization of allenyl indoles will be developed. The Pt-catalyzed hydroamination of alkenyl amines and methodologies for the hydroamination of alkenyl carbamates will also be explored. Additional reactions slated for examination include intramolecular hydroamination of allenes, intermolecular hydroamination of unactivated olefins, Pd-catalyzed cyclization/carboalkoxylation of alkenyl indoles, and Pt-catalyzed hydroalkoxylation of hydroxy olefins. A summer exchange program with North Carolina Central University (NCCU) will bring undergraduate researchers from NCCU to Duke University.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Ross A. Widenhoefer, of the Department of Chemistry at Duke University. Dr. Widenhoefer is exploring new synthetic methods for the conversion of simple organic molecules into more complex molecules containing new carbon-carbon, carbon-nitrogen, and carbon-oxygen bonds. By exploiting the novel chemistry of compounds containing metal atoms, in particular palladium, platinum, and gold, Dr. Widenhoefer is developing simple tools for the construction of complex naturally-occurring and biologically active molecules, with potential applications in the areas of manufacturing, fine chemical production, and pharmaceutical discovery and synthesis. In addition to Duke University students, this research program engages undergraduate students from North Carolina Central University through a summer research exchange program.