Alkene aminations catalysed by transition metals

Abstract

Amines, especially long chain tertiary alkylamines, are industrially useful compounds with a relatively high commercial value. They are currently synthesised by a variety of multi-step processes, but a simple "one pot" catalytic synthesis is a highly desirable alternative with considerable potential advantages over existing methods. This thesis is concerned with possible routes to alkylated amines via amination of alkenes promoted by transition metals. The chemistry of transition metal alkene complexes relevant to amination of the alkene, is reviewed in detail. A search is made for complexes suitable for use as models with which to study the catalytic process. In an attempt to minimise nucleophilic attack at the metal centre, but maximise attack at coordinated alkenes, attempts were made to synthesise complexes containing strongly σ-donating anionic groups. In this context, reactions of palladium compounds with the dianion of N,N'-diphenyloxamide (PhNCOCONPh) are reported, which relate to the synthesis of previously unknown palladium alkene complexes. Also reported are some attempted reactions of amines with known metal alkene complexes.