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Synthesis, characterization, and reactivity of [Pd(phosphine)(py)Cl2] (PEPPSI) and [Pd(phosphine)Cl2]2 complexes

Vladislav Voloshkin (UGent) , Yaxu Liu, Marek Beliš (UGent) , Min Peng (UGent) , Kristof Van Hecke (UGent) , Catherine Cazin (UGent) and Steven Nolan (UGent)
(2023) DALTON TRANSACTIONS. 52(12). p.3690-3698
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Abstract
The synthesis of novel phosphine palladium PEPPSI and dimer complexes bearing RuPhos, SPhos and XPhos phosphines is reported. The crystal structures of XPhos Pd PEPPSI with pyridine, SPhos Pd PEPPSI with 3-chloropyridine as throw-away ligands and the RuPhos palladium dimer were obtained and compared with previously reported congeners. The catalytic activity of these novel complexes was examined via a C-N coupling reaction involving 4-chloroanisole and morpholine. RuPhos complex 2b proved most active, leading to 97% yield with a low (0.2 mol%) catalyst loading, while phosphine palladium dimers showed significantly lower catalytic activity. However, the addition of 3-pentanone as an activator/stabilizer significantly improved the yields of phosphine dimers and PEPPSI complexes when the reactions were performed in THF.
Keywords
HETEROCYCLIC CARBENE COMPLEXES, SUZUKI-MIYAURA, (NHC)PD(ALLYL)CL NHC, PALLADIUM PRECATALYST, CATALYST ACTIVATION, ARYLATION, IPENT

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Citation

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MLA
Voloshkin, Vladislav, et al. “Synthesis, Characterization, and Reactivity of [Pd(Phosphine)(Py)Cl2] (PEPPSI) and [Pd(Phosphine)Cl2]2 Complexes.” DALTON TRANSACTIONS, vol. 52, no. 12, 2023, pp. 3690–98, doi:10.1039/d3dt00293d.
APA
Voloshkin, V., Liu, Y., Beliš, M., Peng, M., Van Hecke, K., Cazin, C., & Nolan, S. (2023). Synthesis, characterization, and reactivity of [Pd(phosphine)(py)Cl2] (PEPPSI) and [Pd(phosphine)Cl2]2 complexes. DALTON TRANSACTIONS, 52(12), 3690–3698. https://doi.org/10.1039/d3dt00293d
Chicago author-date
Voloshkin, Vladislav, Yaxu Liu, Marek Beliš, Min Peng, Kristof Van Hecke, Catherine Cazin, and Steven Nolan. 2023. “Synthesis, Characterization, and Reactivity of [Pd(Phosphine)(Py)Cl2] (PEPPSI) and [Pd(Phosphine)Cl2]2 Complexes.” DALTON TRANSACTIONS 52 (12): 3690–98. https://doi.org/10.1039/d3dt00293d.
Chicago author-date (all authors)
Voloshkin, Vladislav, Yaxu Liu, Marek Beliš, Min Peng, Kristof Van Hecke, Catherine Cazin, and Steven Nolan. 2023. “Synthesis, Characterization, and Reactivity of [Pd(Phosphine)(Py)Cl2] (PEPPSI) and [Pd(Phosphine)Cl2]2 Complexes.” DALTON TRANSACTIONS 52 (12): 3690–3698. doi:10.1039/d3dt00293d.
Vancouver
1.
Voloshkin V, Liu Y, Beliš M, Peng M, Van Hecke K, Cazin C, et al. Synthesis, characterization, and reactivity of [Pd(phosphine)(py)Cl2] (PEPPSI) and [Pd(phosphine)Cl2]2 complexes. DALTON TRANSACTIONS. 2023;52(12):3690–8.
IEEE
[1]
V. Voloshkin et al., “Synthesis, characterization, and reactivity of [Pd(phosphine)(py)Cl2] (PEPPSI) and [Pd(phosphine)Cl2]2 complexes,” DALTON TRANSACTIONS, vol. 52, no. 12, pp. 3690–3698, 2023.
@article{01HQ3EAK47BJD1HWNHHBWQNHZ0,
  abstract     = {{The synthesis of novel phosphine palladium PEPPSI and dimer complexes bearing RuPhos, SPhos and XPhos phosphines is reported. The crystal structures of XPhos Pd PEPPSI with pyridine, SPhos Pd PEPPSI with 3-chloropyridine as throw-away ligands and the RuPhos palladium dimer were obtained and compared with previously reported congeners. The catalytic activity of these novel complexes was examined via a C-N coupling reaction involving 4-chloroanisole and morpholine. RuPhos complex 2b proved most active, leading to 97% yield with a low (0.2 mol%) catalyst loading, while phosphine palladium dimers showed significantly lower catalytic activity. However, the addition of 3-pentanone as an activator/stabilizer significantly improved the yields of phosphine dimers and PEPPSI complexes when the reactions were performed in THF.}},
  author       = {{Voloshkin, Vladislav and Liu, Yaxu and Beliš, Marek and Peng, Min and Van Hecke, Kristof and Cazin, Catherine and Nolan, Steven}},
  issn         = {{1477-9226}},
  journal      = {{DALTON TRANSACTIONS}},
  keywords     = {{HETEROCYCLIC CARBENE COMPLEXES,SUZUKI-MIYAURA,(NHC)PD(ALLYL)CL NHC,PALLADIUM PRECATALYST,CATALYST ACTIVATION,ARYLATION,IPENT}},
  language     = {{eng}},
  number       = {{12}},
  pages        = {{3690--3698}},
  title        = {{Synthesis, characterization, and reactivity of [Pd(phosphine)(py)Cl2] (PEPPSI) and [Pd(phosphine)Cl2]2 complexes}},
  url          = {{http://doi.org/10.1039/d3dt00293d}},
  volume       = {{52}},
  year         = {{2023}},
}
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