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Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes

Chieh-Hung Tien, Matt R. Adams, Michael J. Ferguson, Erin R. Johnson* and Alexander W. H. Speed*

*Department of Chemistry, Dalhousie University, 6274 Coburg Road, P.O. Box 15000, Halifax, Nova Scotia, Canada B3H 4R2, Email: erin.johnsondal.ca, aspeeddal.ca

C.-H. Tien, M. R. Adams, M. J. Ferguson, E. R. Johnson, A. W. H. Speed, Org. Lett., 2017, 19, 5565-5568.

DOI: 10.1021/acs.orglett.7b02695 (free Supporting Information)


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Abstract

1,2,4,3-triazaphospholenes halides catalyze the 1,2 hydroboration of imines and α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate.

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proposed mechanism



Key Words

reduction of imines, pinacolborane, organocatalysis


ID: J54-Y2017