N-Heterocyclic carbenes have been of increased interest to carry out metal-free small molecule activation. Main group heteroatom analogs of carbenes have also been reported to a lesser extent, as they are difficult to synthesize as well as highly reactive with common Lewis bases. We report the synthesis of a novel class of compounds: N-Heterocyclic diazaborolidines as an intramolecular frustrated Lewis acid/base pair (NHB/FLP). These NHB/FLPs possess a 1,3,2-diazaborolidine core as the Lewis acid, with a pendant pyridine group as the Lewis base component. This interaction gives rise to surprising stability when the compounds are exposed to water and molecular oxygen, unlocking new types of chemistry previously unattainable with reactive 3-coordinate boron compounds. We will present the synthesis and characterization of this class of compounds as well as some results of our preliminary reactivity studies.

N-heterocyclic diazaborolidines as frustrated Lewis pairs

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

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.