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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 and Steven Nolan (UGent)
(2007) ADVANCED SYNTHESIS & CATALYSIS. 349(14-15). p.2380-2384
Author
Organization
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

Citation

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MLA
Marion, Nicolas, et al. “N-Heterocyclic Carbene-Palladium Complexes [(NHC)Pd(Acac)Cl] : Improved Synthesis and Catalytic Activity in Large-Scale Cross-Coupling Reactions.” ADVANCED SYNTHESIS & CATALYSIS, vol. 349, no. 14–15, 2007, pp. 2380–84, doi:10.1002/adsc.200700195.
APA
Marion, N., De Fremont, P., Puijk, I. M., Ecarnot, E. C., Amoroso, D., Bell, A., & Nolan, S. (2007). N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl] : improved synthesis and catalytic activity in large-scale cross-coupling reactions. ADVANCED SYNTHESIS & CATALYSIS, 349(14–15), 2380–2384. https://doi.org/10.1002/adsc.200700195
Chicago author-date
Marion, Nicolas, Pierre De Fremont, Iris M Puijk, Elise C Ecarnot, Dino Amoroso, Andrew Bell, and Steven Nolan. 2007. “N-Heterocyclic Carbene-Palladium Complexes [(NHC)Pd(Acac)Cl] : Improved Synthesis and Catalytic Activity in Large-Scale Cross-Coupling Reactions.” ADVANCED SYNTHESIS & CATALYSIS 349 (14–15): 2380–84. https://doi.org/10.1002/adsc.200700195.
Chicago author-date (all authors)
Marion, Nicolas, Pierre De Fremont, Iris M Puijk, Elise C Ecarnot, Dino Amoroso, Andrew Bell, and Steven Nolan. 2007. “N-Heterocyclic Carbene-Palladium Complexes [(NHC)Pd(Acac)Cl] : Improved Synthesis and Catalytic Activity in Large-Scale Cross-Coupling Reactions.” ADVANCED SYNTHESIS & CATALYSIS 349 (14–15): 2380–2384. doi:10.1002/adsc.200700195.
Vancouver
1.
Marion N, De Fremont P, Puijk IM, Ecarnot EC, Amoroso D, Bell A, et al. N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl] : improved synthesis and catalytic activity in large-scale cross-coupling reactions. ADVANCED SYNTHESIS & CATALYSIS. 2007;349(14–15):2380–4.
IEEE
[1]
N. Marion et al., “N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl] : improved synthesis and catalytic activity in large-scale cross-coupling reactions,” ADVANCED SYNTHESIS & CATALYSIS, vol. 349, no. 14–15, pp. 2380–2384, 2007.
@article{8169778,
  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.}},
  author       = {{Marion, Nicolas and De Fremont, Pierre and Puijk, Iris M and Ecarnot, Elise C and Amoroso, Dino and Bell, Andrew and Nolan, Steven}},
  issn         = {{1615-4150}},
  journal      = {{ADVANCED SYNTHESIS & CATALYSIS}},
  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}},
  language     = {{eng}},
  number       = {{14-15}},
  pages        = {{2380--2384}},
  title        = {{N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl] : improved synthesis and catalytic activity in large-scale cross-coupling reactions}},
  url          = {{http://doi.org/10.1002/adsc.200700195}},
  volume       = {{349}},
  year         = {{2007}},
}
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