Highly Active [Pd(μ-Cl)(Cl)(NHC)]2 (NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides

Caroline E. Hartmann; Steven Patrick Nolan; Catherine S.J. Cazin

doi:10.1021/om900072f

Highly Active [Pd(μ-Cl)(Cl)(NHC)]₂ (NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides

Caroline E. Hartmann, Steven Patrick Nolan, Catherine S.J. Cazin

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

72 Citations (Scopus)

Abstract

Cross-coupling reactions of Grignard reagents with functionalized aryl, heteroaryl, and sterically hindered aryl chlorides are reported. A protocol disclosing the coupling of a wide range of substrates using complexes of the type [Pd(mu-Cl)(Cl)(NHC)](2) (NHC = N-heterocyclic carbene) as precatalysts (at low catalyst loading) under mild conditions is presented. The system allows for the synthesis of highly sterically hindered products, including tri- and tetra-ortho-substituted biaryls.

Original language	English
Pages (from-to)	2915-2919
Number of pages	5
Journal	Organometallics
Volume	28
Issue number	9
DOIs	https://doi.org/10.1021/om900072f
Publication status	Published - 11 May 2009

Keywords

RESTRICTED FLEXIBILITY
PALLADIUM CATALYSTS
KUMADA REACTION
BR/MG EXCHANGE
BOND FORMATION
C-C
LIGANDS
COMPLEXES
ALCOHOLS
BROMIDES

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10.1021/om900072f

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title = "Highly Active [Pd(μ-Cl)(Cl)(NHC)]2 (NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides",

abstract = "Cross-coupling reactions of Grignard reagents with functionalized aryl, heteroaryl, and sterically hindered aryl chlorides are reported. A protocol disclosing the coupling of a wide range of substrates using complexes of the type [Pd(mu-Cl)(Cl)(NHC)](2) (NHC = N-heterocyclic carbene) as precatalysts (at low catalyst loading) under mild conditions is presented. The system allows for the synthesis of highly sterically hindered products, including tri- and tetra-ortho-substituted biaryls.",

keywords = "RESTRICTED FLEXIBILITY, PALLADIUM CATALYSTS, KUMADA REACTION, BR/MG EXCHANGE, BOND FORMATION, C-C, LIGANDS, COMPLEXES, ALCOHOLS, BROMIDES",

author = "Hartmann, {Caroline E.} and Nolan, {Steven Patrick} and Cazin, {Catherine S.J.}",

year = "2009",

month = may,

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doi = "10.1021/om900072f",

language = "English",

volume = "28",

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journal = "Organometallics",

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T1 - Highly Active [Pd(μ-Cl)(Cl)(NHC)]2 (NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides

AU - Hartmann, Caroline E.

AU - Nolan, Steven Patrick

AU - Cazin, Catherine S.J.

PY - 2009/5/11

Y1 - 2009/5/11

N2 - Cross-coupling reactions of Grignard reagents with functionalized aryl, heteroaryl, and sterically hindered aryl chlorides are reported. A protocol disclosing the coupling of a wide range of substrates using complexes of the type [Pd(mu-Cl)(Cl)(NHC)](2) (NHC = N-heterocyclic carbene) as precatalysts (at low catalyst loading) under mild conditions is presented. The system allows for the synthesis of highly sterically hindered products, including tri- and tetra-ortho-substituted biaryls.

AB - Cross-coupling reactions of Grignard reagents with functionalized aryl, heteroaryl, and sterically hindered aryl chlorides are reported. A protocol disclosing the coupling of a wide range of substrates using complexes of the type [Pd(mu-Cl)(Cl)(NHC)](2) (NHC = N-heterocyclic carbene) as precatalysts (at low catalyst loading) under mild conditions is presented. The system allows for the synthesis of highly sterically hindered products, including tri- and tetra-ortho-substituted biaryls.

KW - RESTRICTED FLEXIBILITY

KW - PALLADIUM CATALYSTS

KW - KUMADA REACTION

KW - BR/MG EXCHANGE

KW - BOND FORMATION

KW - C-C

KW - LIGANDS

KW - COMPLEXES

KW - ALCOHOLS

KW - BROMIDES

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U2 - 10.1021/om900072f

DO - 10.1021/om900072f

M3 - Article

SN - 0276-7333

VL - 28

SP - 2915

EP - 2919

JO - Organometallics

JF - Organometallics

IS - 9

ER -

Highly Active [Pd(μ-Cl)(Cl)(NHC)]₂ (NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides

Abstract

Keywords

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