Sarah Wengryniuk, Ph.D.

Temple University 

February 5, 2020 (Wed.)
11:00 – 11:50 am
TBD

Turning Reactivity on its Head: Novel Umpolung Strategies Enabled by Hypervalent Iodine Reagents

Abstract:

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 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, our studies towards electrophilic oxygen activation, enone C–H arylation, and “heterocyclic group transfer” reactions will be discussed.