An efficient and mild protocol for the alpha-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system

R Singh; Steven Patrick Nolan

doi:10.1016/j.jorganchem.2005.07.083

An efficient and mild protocol for the alpha-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system

R Singh, Steven Patrick Nolan

Research output: Other contribution

33 Citations (Scopus)

Abstract

The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the alpha-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high activity, allowing for the coupling of non-activated chlorides. The use of hindered substrates provided an avenue for convenient synthesis of various ketone derivatives. The first examples of alpha-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented. (c) 2005 Elsevier B.V. All rights reserved.

Original language	English
Volume	690
DOIs	https://doi.org/10.1016/j.jorganchem.2005.07.083
Publication status	Published - 1 Dec 2005

Keywords

arylation
ketones
arylchlorides
N-heterocyclic carbenes
palladium
N-HETEROCYCLIC-CARBENE
SILYL ENOL ETHERS
CATALYZED COUPLING REACTIONS
REGIOSELECTIVE ARYLATION
CARBONYL-COMPOUNDS
AEROBIC OXIDATION
ORGANIC-SYNTHESIS
BOND FORMATION
ARYL HALIDES
POTASSIUM 2,6-DI-T-BUTYLPHENOXIDE

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10.1016/j.jorganchem.2005.07.083

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title = "An efficient and mild protocol for the alpha-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system",

abstract = "The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the alpha-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high activity, allowing for the coupling of non-activated chlorides. The use of hindered substrates provided an avenue for convenient synthesis of various ketone derivatives. The first examples of alpha-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented. (c) 2005 Elsevier B.V. All rights reserved.",

keywords = "arylation, ketones, arylchlorides, N-heterocyclic carbenes, palladium, N-HETEROCYCLIC-CARBENE, SILYL ENOL ETHERS, CATALYZED COUPLING REACTIONS, REGIOSELECTIVE ARYLATION, CARBONYL-COMPOUNDS, AEROBIC OXIDATION, ORGANIC-SYNTHESIS, BOND FORMATION, ARYL HALIDES, POTASSIUM 2,6-DI-T-BUTYLPHENOXIDE",

author = "R Singh and Nolan, {Steven Patrick}",

year = "2005",

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day = "1",

doi = "10.1016/j.jorganchem.2005.07.083",

language = "English",

volume = "690",

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AU - Singh, R

AU - Nolan, Steven Patrick

PY - 2005/12/1

Y1 - 2005/12/1

N2 - The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the alpha-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high activity, allowing for the coupling of non-activated chlorides. The use of hindered substrates provided an avenue for convenient synthesis of various ketone derivatives. The first examples of alpha-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented. (c) 2005 Elsevier B.V. All rights reserved.

AB - The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the alpha-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high activity, allowing for the coupling of non-activated chlorides. The use of hindered substrates provided an avenue for convenient synthesis of various ketone derivatives. The first examples of alpha-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented. (c) 2005 Elsevier B.V. All rights reserved.

KW - arylation

KW - ketones

KW - arylchlorides

KW - N-heterocyclic carbenes

KW - palladium

KW - N-HETEROCYCLIC-CARBENE

KW - SILYL ENOL ETHERS

KW - CATALYZED COUPLING REACTIONS

KW - REGIOSELECTIVE ARYLATION

KW - CARBONYL-COMPOUNDS

KW - AEROBIC OXIDATION

KW - ORGANIC-SYNTHESIS

KW - BOND FORMATION

KW - ARYL HALIDES

KW - POTASSIUM 2,6-DI-T-BUTYLPHENOXIDE

UR - http://www.scopus.com/inward/record.url?scp=27744568329&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2005.07.083

DO - 10.1016/j.jorganchem.2005.07.083

M3 - Other contribution

VL - 690

ER -

An efficient and mild protocol for the alpha-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system

Abstract

Keywords

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