Catalytic Hydrosilylation of Amides

Sammanfattning: In this thesis, different protocols and approaches are described for thehydrosilylation of tertiary amides to amines or enamines. The development of simple andeffective methods for the production of amines from amides is of great importance to bothacademic and industrial users, since the final product represents a valuable building blockfor fine and bulk chemicals. Furthermore, enamines constitute important starting materialsto a variety of functionalized and complex organic compounds.The first part of the thesis focuses on the development and investigation of acatalytic protocol for the reduction of amides to amines using an inexpensive and efficientiron catalyst together with cost-effective, stable, and non-toxic PMHS(poly(methylhydrosiloxane)) as the hydride source. The active catalytic species was formedin situ by combining Fe(OAc)2 as the iron source and easily synthesized imidazolium salts.The second part deals with a novel transition metal–free catalytic hydrosilylationmethodology for the transformation of amides to the corresponding amines or enamines. Itwas found that nucleophilic activation of the trialkoxysilanes by potassium tert-butoxidefacilitates the reduction of benzylic amides to enamines; aliphatic and benzamides toamines. Furthermore, a simple way to tune the selectivity of the reduction of aliphaticamides was found.