Part I. Transition Metal Cross Coupling with Iminium and Oxocarbenium Ions. Part II. Enantioselective Radiosynthesis of PET Tracers Containing [18F]Fluorohydrins.

Abstract

Part I of this thesis will cover the discovery of a Ni-catalyzed cross coupling reaction between N-acyliminium ions derived from quinoline and isoquinoline-based N,O-acetals and arylboronic acids. A detailed treatment of the optimization of this reaction along with its scope will be presented. Additionally, details of the mechanism through several studies will be presented. Finally, a brief discussion of progress toward rendering this method enantioselective will be considered. The second section of Part I will cover a Ni-catalyzed cross-coupling reaction between oxocarbenium ions derived from chromene acetals and arylboronic acids. A detailed treatment of the optimization of this reaction along with its scope will be presented. Additionally, details of the mechanism through several studies will be presented alongside progress toward rendering this reaction asymmetric.

Part II of this thesis will focus on the development of an enantioselective radiofluorination of epoxides with [18F]fluoride. A brief description of the practical applications of PET will be considered in addition to optimization studies and scope of the developed method.