Economical, Green, and Safe Route Towards Substituted Lactones by Anodic Generation of Oxycarbonyl Radicals

Alessia Petti, Matthew C. Leech, Anthony D. Garcia, Iain C.A. Goodall, Adrian P. Dobbs, Kevin Lam

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A new electrochemical methodology has been developed for the generation of oxycarbonyl radicals under mild and green conditions from readily available hemioxalate salts. Mono- and multi-functionalised γ-butyrolactones were synthesised through exo-cyclisation of these oxycarbonyl radicals with an alkene, followed by the sp3–sp3 capture of the newly formed carbon-centred radical. The synthesis of functionalised valerolactone derivatives was also achieved, demonstrating the versatility of the newly developed methodology. This represents a viable synthetic route towards pharmaceutically important fragments and further demonstrates the practicality of electrosynthesis as a green and economical method to activate small organic molecules.

Original languageEnglish
Pages (from-to)16115-16118
Number of pages4
JournalAngewandte Chemie - International Edition
Volume58
Issue number45
DOIs
Publication statusPublished - Nov 4 2019

Keywords

  • electrochemistry
  • electrosynthesis
  • green chemistry
  • lactones
  • radical cyclisation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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