Transition Metal-Catalyzed Tandem Electrocyclization Migration Reaction Using Styryl Azides

This thesis describes transition metal-catalyzed tandem electrocyclization reaction employing styryl azides as the nitrogen source to form highly functionalized N-heterocycles. Chapter one briefly highlights methods that construct new C–C bond or C–N bond via domino electrocyclization migration reaction. Nazarov reaction, Rantenstrauch rearrangement and transition metal catalyzed electrocyclization migration using styryl azide as nitrogen sources are discussed. In Chapter two, I show that dirhodium(II) carboxylate complex can trigger a preferential aminomethylene [1,2]-shift when exposed to β,β-dimethylene-substituted styryl azides, completing the migratorial aptitude scale. In Chapter three and four, I describe my effort to explore the migration selectivity of ester and how steric environment influence the reaction outcome. I also extend the method to oxindole synthesis. Chapter five describes a way to manipulate the selectivity of sp3 C–H bond amination and electrocycliztion by controlling reaction conditions and functionality on substrates. Using certain catalyst can achieve selective transformation.