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Towards environmentally friendlier Suzuki-Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes

(2018) GREEN CHEMISTRY. 20(14). p.3246-3252
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Abstract
The preparation of [NHC center dot H][Pd(eta(3)-R-allyl)Cl-2] complexes is disclosed and represents a facile, atom-economical, environmentally friendly and rapid synthesis. These palladates are immediate synthetic precursors to the well-known [Pd(NHC)(eta(3)-R-allyl)Cl] complexes. Their activation leading to catalytically relevant species has been studied in the Suzuki-Miyaura reaction. The need for an activation step prior to the catalysis was examined. The reaction scope showcases its ease and breadth in terms of functional group tolerance. Electron-donating and electron-withdrawing aryl chlorides and bromides were coupled effectively as well as heteroatom-containing and sterically hindered aryl halides. The catalytic reaction was conducted in ethanol with a weak and inexpensive inorganic base.
Keywords
CROSS-COUPLING REACTIONS, ORTHO-SUBSTITUTED BIARYLS, ARYL CHLORIDES, (NHC)PD(ALLYL)CL NHC, CATALYTIC-ACTIVITY, SOLVENT SELECTION, ROOM-TEMPERATURE, I COMPLEXES, PRECATALYSTS, LIGANDS

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MLA
Zinser, Caroline M et al. “Towards Environmentally Friendlier Suzuki-Miyaura Reactions with Precursors of Pd-NHC (NHC = N-heterocyclic Carbene) Complexes.” GREEN CHEMISTRY 20.14 (2018): 3246–3252. Print.
APA
Zinser, C. M., Warren, K. G., Meadows, R. E., Nahra, F., Al-Majid, A. M., Barakat, A., Islam, M. S., et al. (2018). Towards environmentally friendlier Suzuki-Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes. GREEN CHEMISTRY, 20(14), 3246–3252.
Chicago author-date
Zinser, Caroline M, Katie G Warren, Rebecca E Meadows, Fady Nahra, Abdullah M Al-Majid, Assem Barakat, Mohammad S Islam, Steven Nolan, and Catherine Cazin. 2018. “Towards Environmentally Friendlier Suzuki-Miyaura Reactions with Precursors of Pd-NHC (NHC = N-heterocyclic Carbene) Complexes.” Green Chemistry 20 (14): 3246–3252.
Chicago author-date (all authors)
Zinser, Caroline M, Katie G Warren, Rebecca E Meadows, Fady Nahra, Abdullah M Al-Majid, Assem Barakat, Mohammad S Islam, Steven Nolan, and Catherine Cazin. 2018. “Towards Environmentally Friendlier Suzuki-Miyaura Reactions with Precursors of Pd-NHC (NHC = N-heterocyclic Carbene) Complexes.” Green Chemistry 20 (14): 3246–3252.
Vancouver
1.
Zinser CM, Warren KG, Meadows RE, Nahra F, Al-Majid AM, Barakat A, et al. Towards environmentally friendlier Suzuki-Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes. GREEN CHEMISTRY. 2018;20(14):3246–52.
IEEE
[1]
C. M. Zinser et al., “Towards environmentally friendlier Suzuki-Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes,” GREEN CHEMISTRY, vol. 20, no. 14, pp. 3246–3252, 2018.
@article{8577727,
  abstract     = {The preparation of [NHC center dot H][Pd(eta(3)-R-allyl)Cl-2] complexes is disclosed and represents a facile, atom-economical, environmentally friendly and rapid synthesis. These palladates are immediate synthetic precursors to the well-known [Pd(NHC)(eta(3)-R-allyl)Cl] complexes. Their activation leading to catalytically relevant species has been studied in the Suzuki-Miyaura reaction. The need for an activation step prior to the catalysis was examined. The reaction scope showcases its ease and breadth in terms of functional group tolerance. Electron-donating and electron-withdrawing aryl chlorides and bromides were coupled effectively as well as heteroatom-containing and sterically hindered aryl halides. The catalytic reaction was conducted in ethanol with a weak and inexpensive inorganic base.},
  author       = {Zinser, Caroline M and Warren, Katie G and Meadows, Rebecca E and Nahra, Fady and Al-Majid, Abdullah M and Barakat, Assem and Islam, Mohammad S and Nolan, Steven and Cazin, Catherine},
  issn         = {1463-9262},
  journal      = {GREEN CHEMISTRY},
  keywords     = {CROSS-COUPLING REACTIONS,ORTHO-SUBSTITUTED BIARYLS,ARYL CHLORIDES,(NHC)PD(ALLYL)CL NHC,CATALYTIC-ACTIVITY,SOLVENT SELECTION,ROOM-TEMPERATURE,I COMPLEXES,PRECATALYSTS,LIGANDS},
  language     = {eng},
  number       = {14},
  pages        = {3246--3252},
  title        = {Towards environmentally friendlier Suzuki-Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes},
  url          = {http://dx.doi.org/10.1039/c8gc00860d},
  volume       = {20},
  year         = {2018},
}

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