Hypervalent iodine reagents in the I(III) oxidation state have emerged as a versatile, environmentally benign toolkit for the functionalization of organic molecules. Amongst their diverse reactivity is the ability to facilitate reversed-polarity, or “umpolung”, transformations of typically nucleophilic functionalities, enabling novel bond disconnections. Our laboratory has leveraged an underexplored class of I(III)-reagents, (bis)cationic nitrogen ligated lambda-3 iodanes (<i>N</i>-HVIs), as a platform to develop umpolung transformations of heteroatoms and alkenes. The presence of datively bound heterocyclic ligands leads to enhanced, highly tunable and novel reactivity relative to their well-established oxygen or halogen ligated counterparts. In this talk, applications to electrophilic oxygen activation, enone C–H arylation, and pyridinium group transfer reactions will be discussed.<br/>

Novel umpolung strategies enabled by hypervalent iodine reagents

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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