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

doi:10.1016/j.tet.2008.05.018

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

63 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 language	English
Pages (from-to)	7437-7443
Journal	Tetrahedron
Volume	64
Issue number	30-31
DOIs	https://doi.org/10.1016/j.tet.2008.05.018
Publication status	Published - 21 Jul 2008

Keywords

2-Bromopyridines
DFT calculations
Palladium catalysis
Suzuki reaction mechanism

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10.1016/j.tet.2008.05.018

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

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. {\textcopyright} 2008 Elsevier Ltd. All rights reserved.",

keywords = "2-Bromopyridines, DFT calculations, Palladium catalysis, Suzuki reaction mechanism",

author = "Cristina Sicre and Braga, {Ataualpa A.C.} and Feliu Maseras and Cid, {M. Magdalena}",

year = "2008",

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T1 - Mechanistic insights into the transmetalation step of a Suzuki-Miyaura reaction of 2(4)-bromopyridines: characterization of an intermediate

AU - Sicre, Cristina

AU - Braga, Ataualpa A.C.

AU - Maseras, Feliu

AU - Cid, M. Magdalena

PY - 2008/7/21

Y1 - 2008/7/21

N2 - 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.

AB - 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.

KW - 2-Bromopyridines

KW - DFT calculations

KW - Palladium catalysis

KW - Suzuki reaction mechanism

U2 - 10.1016/j.tet.2008.05.018

DO - 10.1016/j.tet.2008.05.018

M3 - Article

SN - 0040-4020

VL - 64

SP - 7437

EP - 7443

JO - Tetrahedron

JF - Tetrahedron

IS - 30-31

ER -

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

Abstract

Keywords

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