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

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

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-h...

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Veröffentlicht in:Organic letters 2021-09, Vol.23 (17), p.6617-6621
Hauptverfasser: Clarke, Joshua J, Maekawa, Yuuki, Nambo, Masakazu, Crudden, Cathleen M
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container_title Organic letters
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creator Clarke, Joshua J
Maekawa, Yuuki
Nambo, Masakazu
Crudden, Cathleen M
description 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.
doi_str_mv 10.1021/acs.orglett.1c01892
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title Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane
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