Novel transformations for the synthesis of nitrogen containing carbo- and heterocycles

Adcock, Holly Victoria (2015). Novel transformations for the synthesis of nitrogen containing carbo- and heterocycles. University of Birmingham. Ph.D.

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This thesis details the discovery and development of several novel gold-catalysed reactions for the synthesis of nitrogen containing carbo- and heterocyclic frameworks from carbon-carbon triple bonds. The realisation of a 1,1-carboalkoxylation strategy to generate gold carbenes from ynamides is described. This novel skeletal rearrangement proceeds with a previously unreported nitrogen migration onto a gold carbene for the synthesis of highly functionalised indenes. The mechanism has been investigated using isotopic labelling which confirms the predicted mode of cyclisation, enforced by the electronic properties of ynamides. This work led to the discovery of a gold-catalysed polycyclisation reaction to generate complex three-dimensional tetracyclic products. The scope and limitations of this method are described, and the mechanism has been probed using isotopic labelling. A novel copper-catalysed cascade reaction has also been demonstrated towards the synthesis of valuable nitrogen heterocycles. Finally a gold-catalysed rearrangement of electron deficient alkynes under oxidative conditions is detailed along with the reaction optimisation and difficulties encountered.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: Engineering and Physical Sciences Research Council
Subjects: Q Science > QD Chemistry


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