Stereospecific Palladium-Catalyzed Cross-Coupling of (E)- and (Z)-Alkenylsilanolates with Aryl Chlorides

Scott E. Denmark* and Jeffrey M. Kallemeyn
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801
J. Am. Chem. Soc., 2006, 128 (50), pp 15958–15959
DOI: 10.1021/ja065988x
Publication Date (Web): December 2, 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.

, denmark@scs.uiuc.edu

Abstract

Abstract Image

The cross-coupling of geometrically defined (E)- and (Z)-alkenyl- and styrylsilanolates with a wide variety of aromatic and heteroaromatic chlorides has been achieved. Under catalysis by bulky, biphenyl-derived phosphines and allylpalladium chloride, the (preformed, stable) potassium salts of di-, tri- and tetrasubstituted alkenyldimethylsilanols undergo high yielding and highly stereospecific coupling to aryl chlorides in THF or dioxane. A variety of functional groups are compatible with these reaction conditions including nitro, ester, ketone, and nitrile. Both (E)- and (Z)-alkenylsilanolates coupled with nearly identical rate and efficiency.

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History

  • Published In Issue December 20, 2006
  • Received August 17, 2006

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