Copper-Mediated Chan-Lam Amidation Of Arylboronic Acids

The formation of C-N bonds is of paramount importance within numerous areas of chemistry and appears within a vast array of different molecules.Modern palladium catalysed Buchwald-Hartwig has overcome many of the limitations related to traditional copper catalysed Ullmann and Goldberg coupling such as high temperatures and prolonged reaction times.However,the high expense of palladium as well as its increased sensitivity to deactivation has promoted an increased interest in recent years to classical metal catalysts such as copper.The Chan-Evans-Lam reaction is one such reaction,which utilises copper in the formation of C-N bonds.The reaction has been performed on a wide range of substrates using mild conditions as well as using weaker bases allowing more labile functional groups to be used now meaning it is a vital reaction in modern day organic synthesis.This investigation utilises the Chan-Evans-Lam reaction to produce the coupled aryl amide product.However,unlike commonly described in the literature the reaction does not utilise an amide as the starting material.Instead the nitrile from the solvent MeCN produces the aryl amide product without the presence of a base.An optimisation of this process is hereby presented as well as an investigation into the substrate scope of the reaction using different boronic acid and nitrile substrates.Finally,studies were undertaken in an attempt to understand the mechanism of the reaction.