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

A major interest in synthetic research is the controlled introduction and elaboration of new carbon-heteroatom bonds for the synthesis of arom. and heteroarom. 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 methodol. to activate arom. 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 redn./protection sequence. The products from this technol. provide fundamental building blocks for the prepn. of a variety of pharmacol. important heterocyclic compds. [on SciFinder(R)]