Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride

Mike Butters, Jeremy N. Harvey, Jesus Jover, Alastair J. J. Lennox, Guy C. Lloyd-Jones, Paul M. Murray

Research output: Contribution to journalArticlepeer-review

Abstract

Undercover agents: The biaryl coupling of an aryltrifluoroborate with an aryl bromide involves in situ hydrolysis of the boron reagent. The hydrolysis products are key components in ensuring that the reaction proceeds with high efficiency and avoids the extensive generation of undesired phenolic and homocoupling side products.
Original languageEnglish
Pages (from-to)5156–5160
Number of pages5
JournalAngewandte Chemie International Edition
Volume49
Issue number30
DOIs
Publication statusPublished - 12 Jul 2010

Keywords

  • boron
  • fluorides
  • homogeneous catalysis
  • palladium
  • reaction mechanisms
  • ELECTROPHILIC DISPLACEMENT REACTIONS
  • ARYLBORONIC ACIDS
  • POTASSIUM ARYL
  • ORGANOTRIFLUOROBORATE SALTS
  • PHOSPHINE COMPLEXES
  • ARENEBORONIC ACIDS
  • ALKENYL BROMIDES
  • PALLADIUM
  • REDUCTION
  • CATALYSTS

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