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Modified [(IPr)Pd(R-acac)Cl] complexes : influence of the acac substitution on the catalytic activity in aryl amination

Nicolas Marion, Oscar Navarro, Edwin D Stevens, Elise C Ecarnot, Andrew Bell, Dino Amoroso and Steven Nolan (UGent)
(2010) CHEMISTRY-AN ASIAN JOURNAL. 5(4). p.841-846
Author
Organization
Abstract
The synthesis of a series of [(IPr)Pd(R-acac)Cl] precatalysts (acac=acetylacetonato: IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), where the acac ligand on palladium has been systematically modified through terminal substitution, is reported. The following substituted acac ligands are employed in this study: dibenzoylmethanato (dbm), benzoylacelonato (bac), tetramethylheptanedionato (tmhd), and hexafluoroace tylacetonato (hfac). Full spectroscopic characterization of the new complexes is provided along with X-ray studies for three of these. Investigation of their catalytic activity in cross-coupling is also presented through a comparative study in an aryl amination reaction. The catalytic results show a strong correlation between the increased steric bulk of the acac substituents and an increased activation rate of the precatalyst, going from the acac to the tmhd ligand. This observation, along with the inertness of the Iliac compound, seems to support our previous proposal for the activation mechanism of these complexes under cross-coupling conditions.
Keywords
activation, amination, cross-coupling, N-heterocyclic, carbenes, palladium, CROSS-COUPLING REACTIONS, N-HETEROCYCLIC CARBENE, TEMPERATURE SUZUKI-MIYAURA, ROOM-TEMPERATURE, PALLADIUM(II) COMPLEXES, (NHC)PD(ALLYL)CL NHC, REDUCTIVE ELIMINATION, OXIDATIVE ADDITION, BUCHWALD-HARTWIG, ACETONE DBA

Citation

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MLA
Marion, Nicolas, et al. “Modified [(IPr)Pd(R-Acac)Cl] Complexes : Influence of the Acac Substitution on the Catalytic Activity in Aryl Amination.” CHEMISTRY-AN ASIAN JOURNAL, vol. 5, no. 4, 2010, pp. 841–46, doi:10.1002/asia.200900654.
APA
Marion, N., Navarro, O., Stevens, E. D., Ecarnot, E. C., Bell, A., Amoroso, D., & Nolan, S. (2010). Modified [(IPr)Pd(R-acac)Cl] complexes : influence of the acac substitution on the catalytic activity in aryl amination. CHEMISTRY-AN ASIAN JOURNAL, 5(4), 841–846. https://doi.org/10.1002/asia.200900654
Chicago author-date
Marion, Nicolas, Oscar Navarro, Edwin D Stevens, Elise C Ecarnot, Andrew Bell, Dino Amoroso, and Steven Nolan. 2010. “Modified [(IPr)Pd(R-Acac)Cl] Complexes : Influence of the Acac Substitution on the Catalytic Activity in Aryl Amination.” CHEMISTRY-AN ASIAN JOURNAL 5 (4): 841–46. https://doi.org/10.1002/asia.200900654.
Chicago author-date (all authors)
Marion, Nicolas, Oscar Navarro, Edwin D Stevens, Elise C Ecarnot, Andrew Bell, Dino Amoroso, and Steven Nolan. 2010. “Modified [(IPr)Pd(R-Acac)Cl] Complexes : Influence of the Acac Substitution on the Catalytic Activity in Aryl Amination.” CHEMISTRY-AN ASIAN JOURNAL 5 (4): 841–846. doi:10.1002/asia.200900654.
Vancouver
1.
Marion N, Navarro O, Stevens ED, Ecarnot EC, Bell A, Amoroso D, et al. Modified [(IPr)Pd(R-acac)Cl] complexes : influence of the acac substitution on the catalytic activity in aryl amination. CHEMISTRY-AN ASIAN JOURNAL. 2010;5(4):841–6.
IEEE
[1]
N. Marion et al., “Modified [(IPr)Pd(R-acac)Cl] complexes : influence of the acac substitution on the catalytic activity in aryl amination,” CHEMISTRY-AN ASIAN JOURNAL, vol. 5, no. 4, pp. 841–846, 2010.
@article{8169366,
  abstract     = {{The synthesis of a series of [(IPr)Pd(R-acac)Cl] precatalysts (acac=acetylacetonato: IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), where the acac ligand on palladium has been systematically modified through terminal substitution, is reported. The following substituted acac ligands are employed in this study: dibenzoylmethanato (dbm), benzoylacelonato (bac), tetramethylheptanedionato (tmhd), and hexafluoroace tylacetonato (hfac). Full spectroscopic characterization of the new complexes is provided along with X-ray studies for three of these. Investigation of their catalytic activity in cross-coupling is also presented through a comparative study in an aryl amination reaction. The catalytic results show a strong correlation between the increased steric bulk of the acac substituents and an increased activation rate of the precatalyst, going from the acac to the tmhd ligand. This observation, along with the inertness of the Iliac compound, seems to support our previous proposal for the activation mechanism of these complexes under cross-coupling conditions.}},
  author       = {{Marion, Nicolas and Navarro, Oscar and Stevens, Edwin D and Ecarnot, Elise C and Bell, Andrew and Amoroso, Dino and Nolan, Steven}},
  issn         = {{1861-4728}},
  journal      = {{CHEMISTRY-AN ASIAN JOURNAL}},
  keywords     = {{activation,amination,cross-coupling,N-heterocyclic,carbenes,palladium,CROSS-COUPLING REACTIONS,N-HETEROCYCLIC CARBENE,TEMPERATURE SUZUKI-MIYAURA,ROOM-TEMPERATURE,PALLADIUM(II) COMPLEXES,(NHC)PD(ALLYL)CL NHC,REDUCTIVE ELIMINATION,OXIDATIVE ADDITION,BUCHWALD-HARTWIG,ACETONE DBA}},
  language     = {{eng}},
  number       = {{4}},
  pages        = {{841--846}},
  title        = {{Modified [(IPr)Pd(R-acac)Cl] complexes : influence of the acac substitution on the catalytic activity in aryl amination}},
  url          = {{http://doi.org/10.1002/asia.200900654}},
  volume       = {{5}},
  year         = {{2010}},
}
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