Palladium-catalyzed cross-coupling of <i>gem</i>-difluorocyclopropanes with <i>gem</i>-diborylalkanes: facile synthesis of a diverse array of <i>gem</i>-diboryl-substituted fluorinated alkenes

This study introduces an efficacious palladium-catalyzed method for the regioselective and stereoselective cross-coupling of <i>gem</i>-difluorinated cyclopropanes with an array of <i>gem</i>-diborylalkanes under mild reaction conditions. The innovative methodology facilitates the synthesis of 2-fluoroallylic <i>gem</i>-diboronic esters with exceptional <i>Z</i>-stereo- and chemo-selectivity. Notably, this protocol extended to the ligand-modulated regio- and stereoselectivity divergence cross-coupling of 1,1-difluoro-2-vinylcyclopropane as a reaction partner. Furthermore, we explore further transformations of the fluorinated <i>gem</i>-diboronates, encompassing the oxidation to form ketone and hydrogenation to generate mono-fluorinated alkylated <i>gem</i>-diboronate.