General and mild Ni0-catalyzed α-arylation of ketones using aryl chlorides

Jose Antonio Fernandez Salas; Enrico Marelli; David Bradford Cordes; Alexandra Martha Zoya Slawin; Steven Patrick Nolan

doi:10.1002/chem.201406457

General and mild Ni⁰-catalyzed α-arylation of ketones using aryl chlorides

Jose Antonio Fernandez Salas, Enrico Marelli, David Bradford Cordes, Alexandra Martha Zoya Slawin, Steven Patrick Nolan

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Abstract

A general methodology for the α-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr*)(cin)Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni(NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni⁰/Ni^II catalytic cycle to be at play.

Original language	English
Pages (from-to)	3906-3909
Number of pages	5
Journal	Chemistry - A European Journal
Volume	21
Issue number	10
Early online date	21 Jan 2015
DOIs	https://doi.org/10.1002/chem.201406457
Publication status	Published - 2 Mar 2015

Keywords

Aryl chlorides
Cross-coupling reactions
Ketone arylation
N-heterocyclic carbenes
Nickel
Synthetic methods

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10.1002/chem.201406457

Nolan_2015_ChemEU_General_AM
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Fernández-Salas, J. A., Marelli, E., Cordes, D. B., Slawin, A. M. Z. and Nolan, S. P. (2015), General and Mild Ni0-Catalyzed α-Arylation of Ketones Using Aryl Chlorides. Chem. Eur. J., 21: 3906–3909, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/chem.201406457/abstract
Accepted author manuscript, 685 KB

Cite this

@article{20c287da148c4dc4816b9846c2d797da,

title = "General and mild Ni0-catalyzed α-arylation of ketones using aryl chlorides",

abstract = "A general methodology for the α-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr*)(cin)Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni(NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni0/NiII catalytic cycle to be at play.",

keywords = "Aryl chlorides, Cross-coupling reactions, Ketone arylation, N-heterocyclic carbenes, Nickel, Synthetic methods",

author = "{Fernandez Salas}, {Jose Antonio} and Enrico Marelli and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and Nolan, {Steven Patrick}",

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

year = "2015",

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doi = "10.1002/chem.201406457",

language = "English",

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T1 - General and mild Ni0-catalyzed α-arylation of ketones using aryl chlorides

AU - Fernandez Salas, Jose Antonio

AU - Marelli, Enrico

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Nolan, Steven Patrick

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

PY - 2015/3/2

Y1 - 2015/3/2

N2 - A general methodology for the α-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr*)(cin)Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni(NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni0/NiII catalytic cycle to be at play.

AB - A general methodology for the α-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr*)(cin)Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni(NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni0/NiII catalytic cycle to be at play.

KW - Aryl chlorides

KW - Cross-coupling reactions

KW - Ketone arylation

KW - N-heterocyclic carbenes

KW - Nickel

KW - Synthetic methods

UR - http://onlinelibrary.wiley.com/doi/10.1002/chem.201406457/suppinfo

U2 - 10.1002/chem.201406457

DO - 10.1002/chem.201406457

M3 - Article

C2 - 25611197

SN - 0947-6539

VL - 21

SP - 3906

EP - 3909

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 10

ER -

General and mild Ni⁰-catalyzed α-arylation of ketones using aryl chlorides

Abstract

Keywords

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Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

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

General and mild Ni0-catalyzed α-arylation of ketones using aryl chlorides

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

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

General and mild Ni⁰-catalyzed α-arylation of ketones using aryl chlorides