title: Fluorodecarboxylation for the Synthesis of Trifluoromethyl Aryl Ethers.
abstract: The synthesis of mono-, di-, and trifluoromethyl aryl ethers by fluorodecarboxylation of the corresponding carboxylic acids is reported. AgF2 induces decarboxylation of aryloxydifluoroacetic acids, and AgF, either generated in situ or added separately, serves as a source of fluorine to generate the fluorodecarboxylation products. The addition of 2,6-difluoropyridine increased the reactivity of AgF2 , thereby increasing the range of functional groups and electronic properties of the aryl groups that are tolerated. The reaction conditions used for the formation of trifluoromethyl aryl ethers also served to form difluoromethyl and monofluoromethyl aryl ethers.
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA, 94720, USA.
authors.forename: Qing-Wei
authors.initials: QW
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA, 94720, USA.
authors.forename: Andrew T
authors.initials: AT
authors.lastname: Brusoe
authors.affiliation: Pfizer Inc., Medicinal Sciences, Groton, CT, 06340, USA.
authors.forename: Vincent
authors.initials: V
authors.lastname: Mascitti
authors.affiliation: Pfizer Inc., Medicinal Sciences, Groton, CT, 06340, USA.
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Hesp
authors.affiliation: Pfizer Inc., Medicinal Sciences, Groton, CT, 06340, USA.
authors.forename: David C
authors.initials: DC
authors.lastname: Blakemore
authors.affiliation: Pfizer Inc., Medicinal Sciences, Groton, CT, 06340, USA.
authors.forename: Jeffrey T
authors.initials: JT
authors.lastname: Kohrt
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA, 94720, USA.
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
keywords: arenes; decarboxylation; fluorine; radicals; synthetic methods