N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl]: Improved synthesis and catalytic activity in large-scale cross-coupling reactions

Nicolas Marion; Pierre De Fremont; Iris M. Puijk; Elise C. Ecarnot; Dino Amoroso; Andrew Bell; Steven Patrick Nolan

doi:10.1002/adsc.200700195

N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl]: Improved synthesis and catalytic activity in large-scale cross-coupling reactions

Nicolas Marion, Pierre De Fremont, Iris M. Puijk, Elise C. Ecarnot, Dino Amoroso, Andrew Bell, Steven Patrick Nolan

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

Abstract

From two commercially available starting materials, improved one-step, multigram-scale syntheses of [(IPr)Pd(acac)Cl] [IPr=N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; acac=acetylacetonate] and [(IMes)Pd(acac)Cl] [IMes = N,]Vbis(2,4,6-trimethylphenyl)imidazol-2-ylidene] are described. The catalytic activity of both complexes in cross-coupling reactions has been examined. The most active pre-catalyst, [(IPr)Pd(acac)Cl], has allowed for efficient large-scale (10 mmol) Buch-wald-Hartwig and a-ketone arylation reactions to be carried out.

Original language	English
Pages (from-to)	2380-2384
Number of pages	5
Journal	Advanced Synthesis & Catalysis
Volume	349
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.200700195
Publication status	Published - Oct 2007

Keywords

n-aryl amination
cross-coupling
N-heterocyclic
carbene
a-ketone arylation
large-scale
palladium
SUZUKI-MIYAURA
(NHC)PD(ALLYL)CL NHC
ROOM-TEMPERATURE
ALPHA-ARYLATION
BUCHWALD-HARTWIG
BOND FORMATION
C-N
KETONE
TRANSFORMATIONS
CHEMISTRY

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@article{2dce4ecac6a94cdcb4a6469a91a4acff,

title = "N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl]: Improved synthesis and catalytic activity in large-scale cross-coupling reactions",

abstract = "From two commercially available starting materials, improved one-step, multigram-scale syntheses of [(IPr)Pd(acac)Cl] [IPr=N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; acac=acetylacetonate] and [(IMes)Pd(acac)Cl] [IMes = N,]Vbis(2,4,6-trimethylphenyl)imidazol-2-ylidene] are described. The catalytic activity of both complexes in cross-coupling reactions has been examined. The most active pre-catalyst, [(IPr)Pd(acac)Cl], has allowed for efficient large-scale (10 mmol) Buch-wald-Hartwig and a-ketone arylation reactions to be carried out.",

keywords = "n-aryl amination, cross-coupling, N-heterocyclic, carbene, a-ketone arylation, large-scale, palladium, SUZUKI-MIYAURA, (NHC)PD(ALLYL)CL NHC, ROOM-TEMPERATURE, ALPHA-ARYLATION, BUCHWALD-HARTWIG, BOND FORMATION, C-N, KETONE, TRANSFORMATIONS, CHEMISTRY",

author = "Nicolas Marion and {De Fremont}, Pierre and Puijk, {Iris M.} and Ecarnot, {Elise C.} and Dino Amoroso and Andrew Bell and Nolan, {Steven Patrick}",

year = "2007",

month = oct,

doi = "10.1002/adsc.200700195",

language = "English",

volume = "349",

pages = "2380--2384",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4150",

publisher = "John Wiley & Sons, Ltd",

number = "14-15",

}

TY - JOUR

T1 - N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl]: Improved synthesis and catalytic activity in large-scale cross-coupling reactions

AU - Marion, Nicolas

AU - De Fremont, Pierre

AU - Puijk, Iris M.

AU - Ecarnot, Elise C.

AU - Amoroso, Dino

AU - Bell, Andrew

AU - Nolan, Steven Patrick

PY - 2007/10

Y1 - 2007/10

N2 - From two commercially available starting materials, improved one-step, multigram-scale syntheses of [(IPr)Pd(acac)Cl] [IPr=N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; acac=acetylacetonate] and [(IMes)Pd(acac)Cl] [IMes = N,]Vbis(2,4,6-trimethylphenyl)imidazol-2-ylidene] are described. The catalytic activity of both complexes in cross-coupling reactions has been examined. The most active pre-catalyst, [(IPr)Pd(acac)Cl], has allowed for efficient large-scale (10 mmol) Buch-wald-Hartwig and a-ketone arylation reactions to be carried out.

AB - From two commercially available starting materials, improved one-step, multigram-scale syntheses of [(IPr)Pd(acac)Cl] [IPr=N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; acac=acetylacetonate] and [(IMes)Pd(acac)Cl] [IMes = N,]Vbis(2,4,6-trimethylphenyl)imidazol-2-ylidene] are described. The catalytic activity of both complexes in cross-coupling reactions has been examined. The most active pre-catalyst, [(IPr)Pd(acac)Cl], has allowed for efficient large-scale (10 mmol) Buch-wald-Hartwig and a-ketone arylation reactions to be carried out.

KW - n-aryl amination

KW - cross-coupling

KW - N-heterocyclic

KW - carbene

KW - a-ketone arylation

KW - large-scale

KW - palladium

KW - SUZUKI-MIYAURA

KW - (NHC)PD(ALLYL)CL NHC

KW - ROOM-TEMPERATURE

KW - ALPHA-ARYLATION

KW - BUCHWALD-HARTWIG

KW - BOND FORMATION

KW - C-N

KW - KETONE

KW - TRANSFORMATIONS

KW - CHEMISTRY

UR - http://www.scopus.com/inward/record.url?scp=35948989669&partnerID=8YFLogxK

U2 - 10.1002/adsc.200700195

DO - 10.1002/adsc.200700195

M3 - Article

SN - 1615-4150

VL - 349

SP - 2380

EP - 2384

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 14-15

ER -

N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl]: Improved synthesis and catalytic activity in large-scale cross-coupling reactions

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