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Classical non-catalytic methods such as the Wittig or Horner-Wadsworth-Emmons reaction usually afford poor control over the (E) or (Z) configuration of the C-C double bonds. Catalytic methods for the synthesis of stilbenes have been recently reviewed:
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Asymmetric 1,2-diarylethenes are also prepared by titanium-catalyzed McMurry coupling of aldehydes and ketones or by ruthenium-catalyzed cross-metathesis of vinylarenes, but the first procedure suffers from poor tolerance to functional groups and the second from low selectivities. See, for example:
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2Ar* (Ar* = 3,4-[18-crown-6]-phenyl) produced comparable results In contrast with our observations that short reaction times are key in the efficient synthesis of vinyl derivatives, high yields of 4-vinylacetophenone after 20 h of reaction at 120°C have been reported during the course of our work by Alacid and Nájera using tetrabutylammonium bromide (TBAB) as a nanoparticle stabilizer:
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