Preformed Pd(II) Catalysts based on Monoanionic [N,O] Ligands for Suzuki-Miyaura Cross-Coupling at Low Temperature

Matthew Andrews, Sebastian Brunen, Ruaraidh D. McIntosh, Stephen M. Mansell

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
47 Downloads (Pure)

Abstract

This paper describes the synthesis and catalytic testing of a palladium complex with a 5-membered chelating [N,O] ligand, derived from the condensation of 2,6-diisopropylphenyl aniline and maple lactone. This catalyst was active towards the Suzuki-Miyaura cross-coupling reaction, and its activity was optimised through the selection of base, solvent, catalytic loading and temperature. The optimised conditions are mild, occurring at room temperature and over a short timescale (1 h) using solvents considered to be ‘green’. A substrate scope was then carried out in which the catalyst showed good activity towards aryl bromides with electron-withdrawing groups. The catalyst was active across a broad scope of electron-donating and high-withdrawing aryl bromides with the highest activity shown for weak electron-withdrawing groups. The catalyst also showed good activity across a range of boronic acids and pinacol esters with even boronic acids featuring strong electron-withdrawing groups showing some activity. The catalyst was also a capable catalyst for the cross-coupling of aryl chlorides and phenylboronic acid. This more challenging reaction requires slightly elevated temperatures over a longer timescale but is still considered mild compared to similar examples in the literature.
Original languageEnglish
Article number303
JournalCatalysts
Volume13
Issue number2
Early online date29 Jan 2023
DOIs
Publication statusPublished - Feb 2023

Keywords

  • Suzuki-Miyaura
  • aryl Halide
  • cross-coupling
  • palladium
  • sustainable

ASJC Scopus subject areas

  • Catalysis
  • Environmental Science(all)
  • Physical and Theoretical Chemistry

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