Distinguishing between pathways for transmetalation in Suzuki-Miyaura reactions

Brad P. Carrow, John F. Hartwig

Research output: Contribution to journalArticle

255 Scopus citations

Abstract

We report a systematic study of the stoichiometric reactions of isolated arylpalladium hydroxo and halide complexes with arylboronic acids and aryltrihydroxyborates to evaluate the relative rates of the two reaction pathways commonly proposed to account for transmetalation in the Suzuki-Miyaura reaction. On the basis of the relative populations of the palladium and organoboron species generated under conditions common for the catalytic process and the observed rate constants for the stoichiometric reactions between the two classes of reaction components, we conclude that the reaction of a palladium hydroxo complex with boronic acid, not the reaction of a palladium halide complex with trihydroxyborate, accounts for transmetalation in catalytic Suzuki-Miyaura reactions conducted with weak base and aqueous solvent mixtures.

Original languageEnglish (US)
Pages (from-to)2116-2119
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number7
DOIs
StatePublished - Feb 23 2011

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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