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A simple synthetic route to well-defined [Pd(NHC)Cl(1-tBu-indenyl)] pre-catalysts for cross-coupling reactions

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Abstract
The development of robust, more efficient, general, easily accessible Pd(II)-NHC pre-catalysts remains a key issue in cross-coupling applications. A selection of well-defined, air and moisture stable [Pd(NHC)Cl(1-Bu-t-indenyl)] (NHC=IPr, IPrCl, IMes, SIMes, IPr*) pre-catalysts have been synthesized in good to excellent yields by reacting [Pd(1-Bu-t-indenyl)(mu-Cl)](2) and various NHC.HCl precursors in the presence of the weak base K2CO3 in green acetone. The synthesized Pd(II)-NHC derivatives displayed excellent catalytic activity in classical Suzuki-Miyaura and Buchwald-Hartwig reactions, especially when IPrCl is employed as ancillary ligand. Additionally, in the challenging Suzuki-Miyaura reaction between esters and arylboronic acids, the [Pd(IPr*)Cl(1-Bu-t-indenyl)] complex exhibited the optimum catalytic activity under very mild reaction conditions.
Keywords
Buchwald-Hartwig amination, N-heterocyclic carbene ligands, Palladium indenyl complexes, Suzuki-Miyaura cross-coupling, Weak base route, SUZUKI-MIYAURA REACTION, HETEROCYCLIC CARBENE COMPLEXES, (NHC)PD(ALLYL)CL NHC, GENERAL-METHOD, PD-PEPPSIC-N, PRECATALYST, LIGANDS, PD(I), REACTIVITY

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Citation

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MLA
Liu, Yaxu, et al. “A Simple Synthetic Route to Well-Defined [Pd(NHC)Cl(1-TBu-Indenyl)] Pre-Catalysts for Cross-Coupling Reactions.” EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. 2022, no. 1, 2022, doi:10.1002/ejic.202100840.
APA
Liu, Y., Scattolin, T., Gobbo, A., Beliš, M., Van Hecke, K., Nolan, S., & Cazin, C. (2022). A simple synthetic route to well-defined [Pd(NHC)Cl(1-tBu-indenyl)] pre-catalysts for cross-coupling reactions. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2022(1). https://doi.org/10.1002/ejic.202100840
Chicago author-date
Liu, Yaxu, Thomas Scattolin, Alberto Gobbo, Marek Beliš, Kristof Van Hecke, Steven Nolan, and Catherine Cazin. 2022. “A Simple Synthetic Route to Well-Defined [Pd(NHC)Cl(1-TBu-Indenyl)] Pre-Catalysts for Cross-Coupling Reactions.” EUROPEAN JOURNAL OF INORGANIC CHEMISTRY 2022 (1). https://doi.org/10.1002/ejic.202100840.
Chicago author-date (all authors)
Liu, Yaxu, Thomas Scattolin, Alberto Gobbo, Marek Beliš, Kristof Van Hecke, Steven Nolan, and Catherine Cazin. 2022. “A Simple Synthetic Route to Well-Defined [Pd(NHC)Cl(1-TBu-Indenyl)] Pre-Catalysts for Cross-Coupling Reactions.” EUROPEAN JOURNAL OF INORGANIC CHEMISTRY 2022 (1). doi:10.1002/ejic.202100840.
Vancouver
1.
Liu Y, Scattolin T, Gobbo A, Beliš M, Van Hecke K, Nolan S, et al. A simple synthetic route to well-defined [Pd(NHC)Cl(1-tBu-indenyl)] pre-catalysts for cross-coupling reactions. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY. 2022;2022(1).
IEEE
[1]
Y. Liu et al., “A simple synthetic route to well-defined [Pd(NHC)Cl(1-tBu-indenyl)] pre-catalysts for cross-coupling reactions,” EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. 2022, no. 1, 2022.
@article{8736533,
  abstract     = {{The development of robust, more efficient, general, easily accessible Pd(II)-NHC pre-catalysts remains a key issue in cross-coupling applications. A selection of well-defined, air and moisture stable [Pd(NHC)Cl(1-Bu-t-indenyl)] (NHC=IPr, IPrCl, IMes, SIMes, IPr*) pre-catalysts have been synthesized in good to excellent yields by reacting [Pd(1-Bu-t-indenyl)(mu-Cl)](2) and various NHC.HCl precursors in the presence of the weak base K2CO3 in green acetone. The synthesized Pd(II)-NHC derivatives displayed excellent catalytic activity in classical Suzuki-Miyaura and Buchwald-Hartwig reactions, especially when IPrCl is employed as ancillary ligand. Additionally, in the challenging Suzuki-Miyaura reaction between esters and arylboronic acids, the [Pd(IPr*)Cl(1-Bu-t-indenyl)] complex exhibited the optimum catalytic activity under very mild reaction conditions.}},
  articleno    = {{e202100840}},
  author       = {{Liu, Yaxu and Scattolin, Thomas and Gobbo, Alberto and Beliš, Marek and Van Hecke, Kristof and Nolan, Steven and Cazin, Catherine}},
  issn         = {{1434-1948}},
  journal      = {{EUROPEAN JOURNAL OF INORGANIC CHEMISTRY}},
  keywords     = {{Buchwald-Hartwig amination,N-heterocyclic carbene ligands,Palladium indenyl complexes,Suzuki-Miyaura cross-coupling,Weak base route,SUZUKI-MIYAURA REACTION,HETEROCYCLIC CARBENE COMPLEXES,(NHC)PD(ALLYL)CL NHC,GENERAL-METHOD,PD-PEPPSIC-N,PRECATALYST,LIGANDS,PD(I),REACTIVITY}},
  language     = {{eng}},
  number       = {{1}},
  pages        = {{8}},
  title        = {{A simple synthetic route to well-defined [Pd(NHC)Cl(1-tBu-indenyl)] pre-catalysts for cross-coupling reactions}},
  url          = {{http://doi.org/10.1002/ejic.202100840}},
  volume       = {{2022}},
  year         = {{2022}},
}

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