Investigations into Cu-catalyzed methods for C(sp2)-N-couplings of hydantoins at both nitrogen atoms

Abstract

N,N’-Diarylated hydantoins have previously been difficult to synthesize and a method for a direct N,N’-diarylation does not exist. This thesis describes a carefully investigated one-pot N,N’-diarylation reaction of hydantoin, using diaryliodonium salts. In addition, have the arylation of the nitrogen atoms been explored in two separate steps. In this study we found a direct method for N,N’-diarylating hydantoin. It has been used it to synthesize three molecules, although the outcome of the reaction relies heavily on the aryl group being coupled and the yield varies significantly. The method is time-efficient and mild, but is limited to arylation of hydantoin without substituents at C-5. The Sandtorv group has also found a new method for N-1-arylation of N-3-functionalised hydantoin and the limitations have been investigated in this thesis. Nine molecules have been synthesized with this method and it is vulnerable, in regards to both the coupling partner and the starting material. The method is mild, but therefore also limited to C-5-unsubstituted hydantoins. We acknowledge that the methods have a narrow area of application, but these molecules cannot be synthesized from hydantoins with other methods.