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

(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

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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 349.14-15 (2007): 2380–2384. Print.
APA
Marion, Nicolas, 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.
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): 2380–2384.
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.
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://dx.doi.org/10.1002/adsc.200700195},
  volume       = {349},
  year         = {2007},
}

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