Novel applications of triarylfluoroboranes in organic synthesis

Abstract

The work described in this thesis is concerned with the utilisation of bulky boron-based Lewis acids as catalysts in organic synthesis. Chapter one provides a general introduction towards the bulky boron-based Lewis acids and diazo compounds, wherein their general synthesis, reactivity, and utilisation in the organic synthesis will be discussed in more detail. Furthermore, the introductory part of this thesis will cover frustrated Lewis pairs, including how they can activate small molecules via two different pathways and how such divergent activation was later utilised in the organic synthesis. Chapter two and three will cover the use of tris(pentafluorophenyl)borane as a catalyst for alkenylation and cyclopropenation of diazo esters, wherein the optimisation reactions, substrate scope, and reaction mechanism will be discussed. Lastly, frustrated Lewis pairs mediated cross-coupling reactions of arylacetylenes and aryl esters will be covered together with conducted studies for a determination of the reaction mechanism