Iron-catalyzed C(sp2)-C(sp3) cross-coupling of aryl chlorobenzoates with alkyl grignard reagents

Elwira Bisz, Michal Szostak

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Abstract

Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)-C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)-O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)-O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.

Original languageEnglish (US)
Article number230
JournalMolecules
Volume25
Issue number1
DOIs
StatePublished - Jan 6 2020

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Aryl esters
  • C-O activation
  • Cross-coupling
  • Fe-catalysis
  • Iron
  • Kumada cross-coupling

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