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

Abstract

This study introduces an efficacious palladium-catalyzed method for the regioselective and stereoselective cross-coupling of gem-difluorinated cyclopropanes with an array of gem-diborylalkanes under mild reaction conditions. The innovative methodology facilitates the synthesis of 2-fluoroallylic gem-diboronic esters with exceptional Z-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 gem-diboronates, encompassing the oxidation to form ketone and hydrogenation to generate mono-fluorinated alkylated gem-diboronate.