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

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 −}{C...

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Bibliographic Details
Published in:Tetrahedron 2008-07, Vol.64 (30), p.7437-7443
Main Authors: Sicre, Cristina, Braga, Ataualpa A.C., Maseras, Feliu, Cid, M. Magdalena
Format: Article
Language:English
Subjects:
2-Bromopyridines
DFT calculations
Palladium catalysis
Suzuki reaction mechanism
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Summary: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 −}{C 5H 2RN}(PR 3) 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.05.018