Mechanistic insights into the transmetalation step of a Suzuki-Miyaura reaction of 2(4)-bromopyridines: characterization of an intermediate

Cristina Sicre, Ataualpa A.C. Braga, Feliu Maseras, M. Magdalena Cid

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60 Citations (Scopus)

Abstract

The mechanistic study of the palladium-catalyzed Suzuki-Miyaura cross-coupling between bromophenylpyridine compounds and phenylboronic acid led to the NMR identification of a transient intermediate in the transmetalation step. This species was identified by DFT calculations as a [Pd{Ph-B(OH)3-}{C5H2RN}(PR3)2] complex, containing a boronate ligand coordinated through an oxygen group to the metal center. The fitting of this intermediate within recent mechanistic proposals on the mechanism of transmetalation is discussed. © 2008 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)7437-7443
JournalTetrahedron
Volume64
Issue number30-31
DOIs
Publication statusPublished - 21 Jul 2008

Keywords

  • 2-Bromopyridines
  • DFT calculations
  • Palladium catalysis
  • Suzuki reaction mechanism

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