Iron-catalysed C(sp2)-H borylation enabled by carboxylate activation

Luke Britton, Jamie H. Docherty*, Andrew P. Dominey, Stephen P. Thomas

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron-catalysed C(sp2)-H borylation reactions of furans and thiophenes under blue light irradiation have been developed. Key reaction intermediates have been prepared and characterised, and suggest two mechanistic pathways are in action involving both C-H metallation and the formation of an iron boryl species.

Original languageEnglish
Article number905
JournalMolecules
Volume25
Issue number4
Early online date18 Feb 2020
DOIs
Publication statusE-pub ahead of print - 18 Feb 2020

Keywords

  • Borylation
  • C-H functionalisation
  • Catalysis
  • Iron
  • Photochemistry
  • Pinacolborane

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