title: Synthesis of α-halo-α,α-difluoromethyl ketones by a trifluoroacetate release/halogenation protocol.
abstract: Three series of α-halo-α,α-difluoromethyl ketones are prepared from highly α-fluorinated gem-diols by exploiting the facile release of trifluoroacetate, followed by immediate trapping of the liberated α,α-difluoroenolate with an electrophilic chlorine, bromine, or iodine source. The products are typically isolated in good yields, even in the case of sensitive, α-iodo-α,α-difluoromethyl ketones. Also, we demonstrate that an α-iodo-α,α-difluoromethyl ketone will participate in a copper-promoted reaction to forge a new carbon-carbon bond.
authors: Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, United States.
authors: Jinu P
authors: JP
authors: John
authors: David A
authors: DA
authors: Colby
mesh_terms: D054879:Halogenation; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007659:Ketones; D014269:Trifluoroacetic Acid