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Iron(III)-Catalyzed Chlorination of Activated Arenes
journal contribution
posted on 2017-06-29, 00:00 authored by Mohamed
A. B. Mostafa, Rosalind M. Bowley, Daugirdas T. Racys, Martyn C. Henry, Andrew SutherlandA general
and regioselective method for the chlorination of activated
arenes has been developed. The transformation uses iron(III) triflimide
as a powerful Lewis acid for the activation of N-chlorosuccinimide
and the subsequent chlorination of a wide range of anisole, aniline,
acetanilide, and phenol derivatives. The reaction was utilized for
the late-stage mono- and dichlorination of a range of target compounds
such as the natural product nitrofungin, the antibacterial agent chloroxylenol,
and the herbicide chloroxynil. The facile nature of this transformation
was demonstrated with the development of one-pot, tandem, iron-catalyzed
dihalogenation processes allowing highly regioselective formation
of different carbon–halogen bonds. The synthetic utility of
the resulting dihalogenated aryl compounds as building blocks was
established with the synthesis of natural products and pharmaceutically
relevant targets.
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building blockstriflimidechlorinationActivated ArenesutilityChlorinationnatureregioselective formationpharmaceuticallybondtransformationsynthesisLewis aciddichlorinationchlorosuccinimidephenol derivativesactivationtandemdihalogenated aryl compoundsacetanilideproduct nitrofunginanisoleareneiron-catalyzed dihalogenation processesagent chloroxylenolherbicide chloroxynilregioselective methodtarget compoundsone-potlate-stageaniline