IBX−I2Redox Couple for Facile Generation of IOH and I+: Expedient Protocol for Iodohydroxylation of Olefins and Iodination of Aromatics

IBX is readily reduced to IBA in the presence of molecular iodine in DMSO to generate hypoiodous acid (IOH), which reacts with a variety of olefins as well as alpha,beta-unsaturated ketones leading to their respective iodohydrins with anti stereochemistry. The same redox chemistry in acetonitrile containing TFA produces iodonium ions for facile iodination of a variety of aromatic compounds in respectable isolated yields.