Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes

Liming Zhang and Sergey A. Kozmin*
Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637
J. Am. Chem. Soc., 2004, 126 (33), pp 10204–10205
DOI: 10.1021/ja046586x
Publication Date (Web): August 3, 2004
Copyright © 2004 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.

, skozmin@uchicago.edu

Abstract

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We have described the first Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate.

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History

  • Published In Issue August 25, 2004
  • Received June 10, 2004

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