Pinacol Cross-Coupling Promoted by an Aluminyl Anion

Andrea O'Reilly, Matthew Evans, Claire McMullin, Robin Fulton, Coles Martyn

Research output: Contribution to journalArticlepeer-review

Abstract

A simple sequential addition protocol for the reductive coupling of ketones and aldehydes by a potassium aluminyl grants access to unsymmetrical pinacolate derivatives. Isolation of an aluminium ketyl complex presents evidence for the accessibility of radical species. Product release from the aluminium centre was achieved using an iodosilane, forming the disilylated 1,2-diol and a neutral aluminium iodide, thereby demonstrating the steps required to generate a closed synthetic cycle for pinacol (cross) coupling at an aluminyl anion.
Original languageEnglish
Article numbere202302999
Number of pages11
JournalChemistry - A European Journal
DOIs
Publication statusPublished - 3 Oct 2023

Keywords

  • aldehyde
  • aluminyl
  • cross-coupling
  • ketyl radical
  • pinacol coupling

ASJC Scopus subject areas

  • General Chemistry
  • Catalysis
  • Organic Chemistry

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