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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Stereospecific palladium-catalyzed cross-coupling of (e)- and (z)-alkenylsilanolates with aryl chlorides.

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.[1]

References

  1. Stereospecific palladium-catalyzed cross-coupling of (e)- and (z)-alkenylsilanolates with aryl chlorides. Denmark, S.E., Kallemeyn, J.M. J. Am. Chem. Soc. (2006) [Pubmed]
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