Fluorodesulfurization of Thionobenzodioxoles with Silver(I) Fluoride

  • J Org Chem. 2020 Oct 16;85(20):13298-13305. doi: 10.1021/acs.joc.0c01729.
Josiah J Newton  1  2 ,  Alan J Brooke  2 ,  Bastian Duhamel  3 ,  Jason M Pulfer  2 ,  Robert Britton  1 ,  Chadron M Friesen  2
Affiliations
  • 1. Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada, V5A 1S6.
  • 2. Department of Chemistry, Trinity Western University, Langley, British Columbia, Canada, V2Y 1Y1.
  • 3. Université de Montpellier, Institut Universitaire de Technologie de Montpellier-Sète, 99 Avenue d'Occitanie, 34090 Montpellier, France.
PMID: 32924485 DOI: 10.1021/acs.joc.0c01729
Abstract

Difluorobenzodioxole is an important functional group found in both pharmaceuticals and agrochemicals. The late-stage introduction of this functional group is challenged by typical fluorination conditions of HF and strong oxidants. Here, we demonstrate that a range of difluorobenzodioxoles can be prepared from catechols in two steps through conversion into thionobenzodioxoles, followed by desulfurative fluorination with silver(I) fluoride. These mild reaction conditions are compatible with a variety of functional groups and enable access to a range of functionalized difluorobenzodioxoles.

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