Variations
To improve the yield of the reaction, lithium chloride is often added to the reaction mixture. This reagent stabilizes the intermediate complex formed by the oxidative addition of a catalyst and accelerates the reaction.
Reactivity and specificity of the Stille reaction can be improved by the addition of stoichiometric amounts of Cu(I) or Mn(II) salts.
The cross-coupling reaction can be inhibited by ligands of a high donor number.
In the presence of Cu(I) salts, palladium-on-carbon has been shown to be an effective catalyst.
In the realm of green chemistry a Stille reaction is reported taking place in a low melting and highly polar mixture of a sugar such as mannitol, a urea such as dimethylurea and a salt such as ammonium chloride . The catalyst system is tris(dibenzylideneacetone)dipalladium(0) with triphenylarsine:
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