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

Org Lett

Department of BioMolecular Sciences, University of Mississippi, University, Mississippi 38677, United States.

Published: July 2021

α-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 α-haloketones without any cyclization or rearrangement due to the mild conditions.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8764867PMC
http://dx.doi.org/10.1021/acs.orglett.1c01636DOI Listing

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