Assembly of azaheterocycles via transition metal-catalyzed annulations involving the activation of C-H bonds

Abstract

Transition metal-catalyzed reactions initiated by the activation of C-H bonds have emerged as an especially attractive approach to assemble and modify a large number of compounds. In this context, annulations are particularly interesting since they provide a straightforward approach to heterocyclic structures from readily available precursors. In this PhD thesis, we describe our efforts towards the synthesis of several highly appealing azaheterocycles through the metal-triggered activation of alkenyl and alkyl C-H bonds and annulation with unsaturated partners. Firstly, in chapter I, we descibe an unconventional annulation for the synthesis of indoline scaffolds through a reaction between o-alkenylanilides and alkynes in presence of rhodium catalysis. Then, in chapter II, we show our attempts towards the synthesis of analogous aliphatic products, azepines, through the employment of homoallylamides as substrates. Finally, in chapter III, we assemble 2- piperidones by the use of alkyl amides and dienes as coupling partners via formal (4+2) cycloadditions in presence of a palladium catalyst.