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Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane.

Joshua J ClarkeYuuki MaekawaMasakazu NamboCathleen M Crudden
Published in: Organic letters (2021)
Mesoionic carbene-stabilized borenium ions efficiently reduce substituted pyridines to piperidines in the presence of a hydrosilane and a hydrogen atmosphere. Control experiments and deuterium labeling studies demonstrate reversible hydrosilylation of the pyridine, enabling full reduction of the N-heterocycle under milder conditions. The silane is a critical reaction component to prevent adduct formation between the piperidine product and the borenium catalyst.
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