Arylation of<i>gem</i>-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination
Kedong Yuan, Taisiia Feoktistova, Paul Ha‐Yeon Cheong, Ryan A. Altman
Abstract
-difluoroalkenes using arylsulfonyl chlorides to deliver α,α-difluorobenzyl products. The reaction proceeds through a β,β-difluoroalkyl-Pd intermediate that typically undergoes unimolecular β-F elimination to deliver monofluorinated alkene products in a net C-F functionalization reaction. However to avoid β-F elimination, we offer the β,β-difluoroalkyl-Pd intermediate an alternate low-energy route involving β-H elimination to ultimately deliver difluorinated products in a net arylation/isomerization sequence. Overall, this reaction enables exploration of new reactivities of unstable fluorinated alkyl-metal species, while also providing new opportunities for transforming readily available fluorinated alkenes into more elaborate substructures.