Mechanism of Cu-catalyzed iododeboronation: a description of ligand-enabled transmetalation, disproportionation, and turnover in Cu-mediated oxidative coupling reactions

Matthew Andrews, Ambre Charpentier, Alexandra Martha Zoya Slawin, Stuart Macgregor, David Bradford Cordes, Allan John Bell Watson*

*Corresponding author for this work

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Abstract

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
Volume13
Issue number16
Early online date7 Aug 2023
DOIs
Publication statusPublished - 18 Aug 2023

Keywords

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

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