DEVELOPMENT OF NEW CATALYTIC SYSTEMS FOR TRANSITION METAL CATALYZED TRANSFER HYDROGENATION OF IMINES AND AMINATION OF ALCOHOLS

Abstract

Amines and their derivatives are of great importance in modern society due to their wide application in pharmaceutical industry, agrochemical industry and other areas. Among the various ways for amine preparation, our group is particularly attracted by transfer hydrogenation of imines and direct amination of alcohols. This thesis mainly contained three parts. 1) The influence of the alcohol as the hydrogen donor on the efficiency and enantioselectivity of Ir-catalyzed asymmetric transfer hydrogenation of imines was discovered. Both experimental and computational studies pointed to the reaction pathway that involved iridium-alkoxide as the reducing species. 2) Knolker’s Fe complex was applied into reactions of transfer hydrogenation of imines as well as aminiation of alcohols. The addition of proper Lewis acids was demonstrated to be the key in achieving good reactivity. 3) Modifications on Shvo’s catalyst were conducted in order to develop its chiral versions. Various planar chiral Shvo-type catalysts were synthesized and tested in transfer hydrogenation reactions.