Evolution of N-Heterocycle-substituted Iodoarenes (NHIAs) to efficient Organocatalysts in Iodine(I/III)-mediated Oxidative Transformations

We herein describe the development of N-heterocycle-stabilized iodoarenes (NHAIs) as oxidation catalysts for oxidative C-X-bond forming reactions. Modification of the N-heterocycle as stabilizing donor in combination with an additional ortho-methoxylation of the iodoarene finally gives organocatalysts that can be applied in the alpha-oxytosylation of ketones even with catalyst loadings as low as 1 mol%.