Mechanism of Cu-Catalyzed Iododeboronation: A Description of Ligand-Enabled Transmetalation, Disproportionation, and Turnover in Cu-Mediated Oxidative Coupling Reactions

Matthew J. Andrews, Ambre Carpentier, Alexandra M. Z. Slawin, David B. Cordes, Stuart A. Macgregor, Allan J. B. Watson

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We report a combined experimental and computational study of the mechanism of the Cu-catalyzed arylboronic acid iododeboronation reaction. A combination of structural and density functional theory (DFT) analyses has allowed determination of the identity of the reaction precatalyst with insight into each step of the catalytic cycle. Key findings include a rationale for ligand (phen) stoichiometry related to key turnover events─the ligand facilitates transmetalation via H-bonding to an organoboron boronate generated in situ and phen loss/gain is integral to the key oxidative events. These data provide a framework for understanding ligand effects on these key mechanistic processes, which underpin several classes of Cu-mediated oxidative coupling reactions.
Original languageEnglish
Pages (from-to)11117-11126
Number of pages10
JournalACS Catalysis
Issue number16
Early online date7 Aug 2023
Publication statusPublished - 18 Aug 2023


  • Cu-catalyzed iododeboronation
  • Cu-mediated oxidative coupling reactions
  • DFT analyses

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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