Intermolecular Heck-type coupling of aryl iodides and allylic acetates.

Org Lett

Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.

Published: October 2005

AI Article Synopsis

  • A palladium-catalyzed reaction can couple allylic acetates with aryl groups, leading to products similar to those obtained through Heck coupling.
  • The best results were achieved using ligand-free palladium on carbon combined with tetrabutylammonium chloride, a trialkylamine base, and water.
  • This method highlights a potentially simpler approach for synthesizing complex organic molecules without the need for additional ligands.

Article Abstract

[reaction: see text] A palladium-catalyzed arylation of allylic acetates followed by beta-acetoxy elimination was shown to produce Heck-type coupling products. Optimal reaction conditions employed ligand-free palladium on carbon in the presence of tetrabutylammonium chloride, a trialkylamine base, and water.

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http://dx.doi.org/10.1021/ol051947eDOI Listing

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