META-ARYL · Changing the rules for aromatic substitution reactions: Development of a general meta-selective copper-catalyzed C–H bond functionalization strategy

This proposal details a new Cu(II) catalysed reactivity concept that will enable the selective C–H bond functionalisation of an important class of aromatic compounds. In particular, a meta-selective C–H arylation of arylacetamides will be the focus of this study. Furthermore, this strategy could also be used to assemble the potent antibiotic, arylomycin A2 as well as facilitate the convenient synthesis of analogues that could be used to probe bacterial resistance, leading to new antibiotic treatments. Our preliminary studies have suggested that this type of transformation is viable for the C–H functionalisation of indoles, acetanilides and anisoles. The capacity to selectively functionalise the C–H bonds of a simple, or complex molecule will be a powerful tool for chemical synthesis and could impact on treatment of diseases.