Nickel-Catalyzed Coupling of Alkenes, Aldehydes, and Silyl Triflates

Sze-Sze Ng, Chun-Yu Ho, and Timothy F. Jamison*
Contribution from the Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2006, 128 (35), pp 11513–11528
DOI: 10.1021/ja062866w
Publication Date (Web): August 10, 2006
Copyright © 2006 American Chemical Society
*

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

, tfj@mit.edu

Abstract

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A full account of two recently developed nickel-catalyzed coupling reactions of alkenes, aldehydes, and silyl triflates is presented. These reactions provide either allylic alcohol or homoallylic alcohol derivatives selectively, depending on the ligand employed. These processes are believed to be mechanistically distinct from Lewis acid-catalyzed carbonyl-ene reactions, and several lines of evidence supporting this hypothesis are discussed.

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History

  • Published In Issue September 06, 2006
  • Received April 25, 2006

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