Iron-catalyzed synthesis of NH sulfoximines and cyclic sulfoximines

In this thesis, the development of iron-catalyzed imidation reactions of sulfoxides to access NH sulfoximines and cyclic sulfoximines is described. The first part of this thesis focused on the iron-catalyzed direct synthesis of NH sulfoximines from sulfoxides. Using a readily available, shelf-stable hydroxylamine triflic acid salt as an imidating agent, a series of free NH sulfoximines were synthesized without additional oxidant. Being aware that most sulfoximines with relevance for crop protection or medical applications contain heterocycles, the approach was also extended to prepare NH sulfoximines with heteroaromatic substituents. The second part of this thesis focused on the iron-catalyzed synthesis of cyclic sulfoximines. The resulting cyclic products are three-dimensional heterocycles, which are important molecular scaffolds in medical and agricultural chemistry. Using a commercially available FeII phthalocyanine (FeIIPc) as catalyst and alkyl azides as nitrene precursors, intramolecular imidation of azido-containing sulfoxides was developed to access various monocyclic and bicyclic sulfoximines. The method feathers a broad functional group tolerance and the resulting three-dimensional heterocycles can be modified by metal-catalyzed cross-coupling reactions