4.5 Article

Multifunctional 2-and 3-Fluoropyrroles

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 13, Pages 2339-2343

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900185

Keywords

Fluoroheterocycles; Selective fluorination; Fluoropyrrole; Electrophilic fluorination; Nitrogen heterocycles

Funding

  1. EPSRC (Durham University DTA)

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Sequential reaction cascades for the synthesis of polysubstituted 2- and 3-fluoropyrrole derivatives from common polybromopyrrole precursors have been developed. A strategic variation of a combination of regioselective debromolithiation followed by trapping of the corresponding carbanions by electrophilic fluorination and Pd catalysed cross-coupling reactions allows access to polyfunctional fluoropyrrole products by methodology applicable to drug discovery programs, extending the range of five-membered fluoroazaheteroaromatic derivatives potentially available for incorporation into screening libraries.

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