Synthesis of Difluorinated Halohydrins by the Chemoselective Addition of Difluoroenolates to α-Haloketones

alpha-Haloketones are valuable intermediates in the synthesis of pharmaceuticals and natural products because they display two electrophiles. Although chemoselective additions to each of these functional groups are known, the use of fluorinated nucleophiles has not been characterized, except for the dimerization of fluorohalomethyl ketones. Our studies demonstrate the use of difluoroenolates to create difluorinated bromohydrins and chlorohydrins from alpha-haloketones without any cyclization or rearrangement due to the mild conditions.

Automated summary

This study demonstrates the use of difluoroenolates to synthesize difluorinated bromohydrins and chlorohydrins from alpha-haloketones under mild conditions without any cyclization or rearrangement.