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

Rohit Singh; Steven P. Nolan

doi:10.1016/j.jorganchem.2005.07.083

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

Rohit Singh, Steven P. Nolan

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

33 Scopus citations

Abstract

The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the α-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 α-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented.

Original language	English (US)
Pages (from-to)	5832-5840
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	24-25
DOIs	https://doi.org/10.1016/j.jorganchem.2005.07.083
State	Published - Dec 1 2005
Externally published	Yes

Bibliographical note

Funding Information:
The National Science Foundation is gratefully acknowledged for financial support of this work and Umicore AG is gratefully acknowledged for the generous gift of Pd(OAc) 2 . We are also grateful to Boehringer-Ingelheim Pharmaceuticals Inc. for an unrestricted grant.

Keywords

Arylation
Arylchlorides
Ketones
N-heterocyclic carbenes
Palladium

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title = "An efficient and mild protocol for the α-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 α-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 α-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented.",

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note = "Funding Information: The National Science Foundation is gratefully acknowledged for financial support of this work and Umicore AG is gratefully acknowledged for the generous gift of Pd(OAc) 2 . We are also grateful to Boehringer-Ingelheim Pharmaceuticals Inc. for an unrestricted grant. ",

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AU - Singh, Rohit

AU - Nolan, Steven P.

N1 - Funding Information: The National Science Foundation is gratefully acknowledged for financial support of this work and Umicore AG is gratefully acknowledged for the generous gift of Pd(OAc) 2 . We are also grateful to Boehringer-Ingelheim Pharmaceuticals Inc. for an unrestricted grant.

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N2 - The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the α-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 α-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented.

AB - The activity of well-defined N-heterocyclic carbene (NHC)-palladium acetate complexes has been studied in the α-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 α-arylation of ketones at room temperature mediated by an NHC-ligated catalyst are also presented.

KW - Arylation

KW - Arylchlorides

KW - Ketones

KW - N-heterocyclic carbenes

KW - Palladium

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ER -

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

Abstract

Bibliographical note

Keywords

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