(Z)-1-Bromo-1-alkenylboronate esters easily prepared by the literature procedures, readily react with aryl magnesium bromide  in ether at -78 oC for 1 h to provide the corresponding �ate� complexes. These �ate� complexes  then undergo the migration of the aryl group from boron to the adjacent carbon provoding (E)-trisubstituted alkenyl boronate esters containing the moiety. It was then subjected to Suzuki coupling in the presence of potassium carbonate and tetrakis (triphenylphosphine) palladium in DMF to provide the products. These products are obtained in 65%-78% yields.  These products are then purified by column chromatography over  alumina  and the structures of these compounds are  confirmed by  NMR spectral data.

New diastereoselective synthesis of (Z) or (E)-trisubstituted alkenes containing  aromatic moieties

244th National Meeting (2012)

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