Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

Enrico Marelli; Martin Michel Alfred Eton Corpet; Sian Davies; Steven Patrick Nolan

doi:10.1002/chem.201404900

Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

Enrico Marelli, Martin Michel Alfred Eton Corpet, Sian Davies, Steven Patrick Nolan

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

Abstract

A general catalytic protocol for the a-arylation of aryl ketones has been developed. It involves the use of a preformed, bench-stable Pd–N-heterocyclic carbene precatalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre-catalyst was also successfully tested in the synthesis of an industrially relevant compound.

Original language	English
Pages (from-to)	17272-17276
Number of pages	5
Journal	Chemistry - A European Journal
Volume	20
Issue number	52
Early online date	20 Nov 2014
DOIs	https://doi.org/10.1002/chem.201404900
Publication status	Published - 22 Dec 2014

Keywords

Catalysts
Ketone arylation
Monodentate ligands
NHC
Palladium

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10.1002/chem.201404900

Nolan_2015_Chem_Ketone_AM
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Marelli, E., Corpet, M., Davies, S. R. and Nolan, S. P. (2014), Palladium-Catalyzed α-Arylation of Arylketones at Low Catalyst Loadings. Chem. Eur. J., 20: 17272–17276, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/chem.201404900/abstract
Accepted author manuscript, 540 KB

Cite this

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title = "Palladium-catalyzed α-arylation of arylketones at low catalyst loadings",

abstract = "A general catalytic protocol for the a-arylation of aryl ketones has been developed. It involves the use of a preformed, bench-stable Pd–N-heterocyclic carbene precatalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre-catalyst was also successfully tested in the synthesis of an industrially relevant compound.",

keywords = "Catalysts, Ketone arylation , Monodentate ligands , NHC, Palladium",

author = "Enrico Marelli and Corpet, {Martin Michel Alfred Eton} and Sian Davies and Nolan, {Steven Patrick}",

note = "The authors thank the ERC (Advanced Researcher award-FUNCAT), 7th Framework Program NMP2-LA-2010–246461 (SYNFLOW) and King Saud University for funding.",

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doi = "10.1002/chem.201404900",

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T1 - Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

AU - Marelli, Enrico

AU - Corpet, Martin Michel Alfred Eton

AU - Davies, Sian

AU - Nolan, Steven Patrick

N1 - The authors thank the ERC (Advanced Researcher award-FUNCAT), 7th Framework Program NMP2-LA-2010–246461 (SYNFLOW) and King Saud University for funding.

PY - 2014/12/22

Y1 - 2014/12/22

N2 - A general catalytic protocol for the a-arylation of aryl ketones has been developed. It involves the use of a preformed, bench-stable Pd–N-heterocyclic carbene precatalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre-catalyst was also successfully tested in the synthesis of an industrially relevant compound.

AB - A general catalytic protocol for the a-arylation of aryl ketones has been developed. It involves the use of a preformed, bench-stable Pd–N-heterocyclic carbene precatalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre-catalyst was also successfully tested in the synthesis of an industrially relevant compound.

KW - Catalysts

KW - Ketone arylation

KW - Monodentate ligands

KW - NHC

KW - Palladium

UR - http://onlinelibrary.wiley.com/doi/10.1002/chem.201404900/suppinfo

U2 - 10.1002/chem.201404900

DO - 10.1002/chem.201404900

M3 - Article

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VL - 20

SP - 17272

EP - 17276

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 52

ER -

Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

Abstract

Keywords

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LSI Collaborative Project: SYNFLOW: EU FP7 Collaborative Project 'SYNFLOW'

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis

Cite this

Palladium-catalyzed α-arylation of arylketones at low catalyst loadings

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

LSI Collaborative Project: SYNFLOW: EU FP7 Collaborative Project 'SYNFLOW'

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis

Cite this