(Z)-Alpha-bromo-1-alkenylboronate esters readily react with 4-methoxyphenyl magnesium bromide in ether at low temperature. After stirring at room temperature, the reaction provides (E)-1-methoxyiphenyl alkenyl boronate esters. It is then reacted with 1-bromo-1-alkynes under Suzuki Coupling conditions in the presence of potassium carbonate, dimrthyl formamide, and tetrakis(triphenylphophine)palladium under reflux con After workup, the corresponding (E)-trisubstituted alkenes containing 4-methoxyphenylland alkyne moieties. The products s are obtained in 72%-80% yields. They are purified by column chromatography over alumina and the structures are confirmed by NMR spectral data.

Highly diastereoselective synthesis of (Z)trisubstituted alkenes containing 4-methoxyphenyl and alkyne moieties via organoboranes

ACS Fall 2021

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