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Letter

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

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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

Org. Lett., 2000, 2 (24), pp 3921–3923

DOI: 10.1021/ol006695q

Publication Date (Web): November 10, 2000

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, wpiers@ucalgary.ca

Abstract

A broad range of benzaldimines and ketimines can be hydrosilated efficiently, employing B(C₆F₅)₃ as a catalyst in conjunction with PhMe₂SiH. 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.

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History

Published In Issue November 30, 2000
Received October 5, 2000

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Letter

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