B(C₆F₅)₃-Catalyzed Hydrosilation of Imines via Silyliminium Intermediates

James M. Blackwell, Eric R. Sonmor, Tiziana Scoccitti and Warren E. Piers*

Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 Canada, Email: wpiersucalgary.ca

J. M. Blackwell, E. R. Sonmor, T. Scoccitti, W. E. Piers, Org. Lett., 2000, 2, 3921-3923.

DOI: 10.1021/ol006695q

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Abstract

Various benzaldimines and ketimines can be hydrosilated efficiently with PhMe₂SiH employing B(C₆F₅)₃ as a catalyst. Spectral evidence supports the intermediacy of a silyliminium cation with a hydridoborate counterion formed via abstraction of a hydride from PhMe₂SiH by B(C₆F₅)₃ in the presence of imines.

see article for more examples

 

proposed mechanism

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Key Words

Hydrosilation, Reduction of Imines, Silanes

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ID: J54-Y2000-360