Metal-free C–H functionalization strategies for heterocyclic building blocks

ORGN 723

Achim Porzelle, achim_porzelle@gmx.de and Nicholas C O Tomkinson, tomkinsonnc@cardiff.ac.uk. School of Chemistry, Cardiff University, Park Place, Main Building, CF10 3AT Cardiff, United Kingdom
A major interest in synthetic research is the controlled introduction and elaboration of new carbon–heteroatom bonds for the synthesis of aromatic and heteroaromatic scaffolds. Recently, C–H functionalization strategies have provided important contributions to the available methods. Although efficient and practical, the majority of these processes rely on activation with transition metals. The development of a metal-free methodology to activate aromatic rings would significantly augment the available methods and provide a valuable synthetic alternative. Within the poster we present a versatile rearrangement strategy to form new aryl-heteroatom bonds providing access to hydroxyl-, amino- and mercapto-anilines. The N-aryl hydroxylamine substrates for the rearrangement process (1) can easily be accessed from nitroarenes through a one-pot reduction/protection sequence. The products from this technology provide fundamental building blocks for the preparation of a variety of pharmacologically important heterocyclic compounds.