Organic Chemistry Seminar
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 (N-HVIs), as well as the analogous I(V) class (Bi(N)-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 the talk, our efforts in reagent development as well as umpolung C–O, C–C, and C–N bond forming reactions towards scaffolds of synthetic and biological relevance will be discussed.