Hydroxyl-directed C–C bond activation of benzophenones for the O-acylation of phenols

Connie Bader, Siri Bruhn, Letitia J. Yao, Christopher J. Douglas

Research output: Contribution to journalArticlepeer-review


We report that 2-hydroxyl benzophenones can be converted to phenyl salicylate esters by loss of an aryl group and O-acylation of the phenols. Iridium, cyclooctadiene, and bulky monodentate phosphine ligands catalyze the ketone C–C bond activation and fragmentation. We identified common side products in this process, which include C-acylation of the phenol reactant or trapping on cyclooctadiene. Several of the processes reported here appear to be under equilibrium control. Overall, our report provides insight into the activation and functionalization of unstrained C–C bonds with group 9 catalysts.

Original languageEnglish (US)
Article number133074
StatePublished - Dec 3 2022

Bibliographical note

Funding Information:
We thank the National Science Foundation , Graduate Research Fellowship program, Grant No. 00039202 to CBA and the University of Minnesota – Twin Cities Lando Program for a summer research fellowship to SB. We thank colleagues Michael Grillo (UMN) for assistance in acquiring high field 13 C NMR data and Hannah Holst (UMN) for assistance with purification of several samples.

Publisher Copyright:
© 2022


  • Benzophenones
  • C–C bond Activation
  • Iridium
  • Mechanism


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