Electrically Driven N(sp 2)- C(sp 2/3) Bond Cleavage of Sulfonamides

Annica Wetzel, Alan M. Jones

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)
120 Downloads (Pure)

Abstract

Sulfonamides are a privileged class of functional groups in medicinal chemistry and an important class of protecting groups in organic synthesis. We report the discovery and development of unexpected electrically driven N(sp2)-C(sp2) and N(sp2)-C(sp3) bond cleavage reactions alongside a dehydrogenative C-O bond coupling reaction under batch and electroflow conditions. Intra-molecular trapping experiments with the diuretic hydrochlorothiazide gave insight into the intermediacy of an N-sulfonyliminium ion en route to the related drug metabolite, chlorothiazide. Using only electrons as the oxidant, this is a green and sustainable technological advancement for sulfonamide deprotection chemistry and drug metabolism studies.

Original languageEnglish
Pages (from-to)3487-3493
Number of pages7
JournalACS Sustainable Chemistry & Engineering
Volume8
Issue number8
Early online date10 Feb 2020
DOIs
Publication statusPublished - 2 Mar 2020

Keywords

  • Electrosynthesis
  • Dealkylation
  • Sulfonamide
  • Oxidation
  • Shono
  • Dehydrogenative Coupling

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

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