Applications of Copper-Boryl Reagents in Synthesis

Abstract

Previous work into the copper catalysed borylation of alkenyl halides has resulted in the synthesis of cyclic Bpin esters. To date however, the reaction has not been applied to the synthesis of saturated heterocycles nor substituted carbocycles.

An overview of the literature precedent for reactions involving copper-boryl complexes is provided in the introduction (chapter 1). Investigations into the reaction were undertaken in an attempt to further expand its scope, and the second chapter outlines preliminary results and investigations into the formation of carbocyclic boronate esters. Application of the borylative cyclisation reaction towards the synthesis of heterocyclic boronate esters is also discussed. The third chapter outlines the development of a copper-boryl mediated deallylation reaction, which was developed as a novel method for the selective deprotection of aryl allyl ethers. Attempts to synthesise chromanyl boronate esters are described in chapter 4,followed by conclusions (chapter 5) and experimental data (chapter 6).