(Z)-Alpha-bromo-1-alkenylboronate esters readily react with 4-biphnylmagnesium bromide in ether at low temperature. After stirring at room temperature, the reaction provides (E)-1-biphenyl alkenyl boronate esters. It is then reacted with 4-fluorophenyl magnesium bromide followed by treatment with iodine in tetrahydrofuran at low temperature. After workup, the corresponding iE)-trisubstituted alkenes containing biphenyl land 4-fluorophenyl 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 (E)trisubstituted alkenes containing 4-fluorophenyl and biphenyl moieties via organoboranes

ACS Spring Meeting 2021

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