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[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride

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Synonym(s):
(4,4′-dtbbpy)NiCl2
Empirical Formula (Hill Notation):
C18H24Cl2N2Ni
CAS Number:
Molecular Weight:
398.00

form

powder or crystals

reaction suitability

core: nickel
reaction type: Cross Couplings
reagent type: catalyst

mp

>300 °C

SMILES string

CC(C1=CC(C2=CC(C(C)(C)C)=CC=N2)=NC=C1)(C)C.Cl[Ni]Cl

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911534904937903019
vibrant-m

911534

(4,4′-dMeObpy)NiCl2

form

powder or crystals

form

powder or crystals

form

powder or crystals

form

powder or crystals

mp

>300 °C

mp

>300 °C

mp

107.9-132.4 °C (Decomp)

mp

>300 °C

Application

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride can be used as a catalyst in:
  • Decarboxylative arylation of oxo acids.
  • Acylation of ethers.
  • Cross-coupling of aryl bromides with alcohols.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Aryl Ketones as Single-Electron-Transfer Photoredox Catalysts in Nickel-Catalyzed the Homocoupling of Aryl Halides
Masuda Y, et al.
European Journal of Organic Chemistry, 5822-5825 (2016)
Photocatalytic α-Acylation of Ethers
Sun Z, et al.
Organic Letters, 19, 3727-3730 (2017)
Ir III/Ni II-Metallaphotoredox catalysis: the oxidation state modulation mechanism versus the radical mechanism
Zhu B, et al.
Chemical Communications (Cambridge, England), 54, 5968-5971 (2018)
Merging photoredox and nickel catalysis: The direct synthesis of ketones by the decarboxylative arylation of α-oxo acids
Chu L, et al.
Angewandte Chemie (International ed. in English), 127, 8040-8044 (2015)
Martins S Oderinde et al.
The Journal of organic chemistry, 80(15), 7642-7651 (2015-07-04)
In order to achieve reproducibility during iridium-photoredox and nickel dual-catalyzed sp(3)-sp(2) carbon-carbon bond-forming reactions, we investigated the role that molecular oxygen (O2), solvent and light-source (CF lamp or blue LED) play in a variety of Ir-photoredox mediated transformations. The presence

Articles

Nickel transition metal and its complexes can be used as a catalyst in many synthetic transformations, like oxidative addition, C-H activation, reductive elimination, oxidative cyclization, oligomerization, and in cross-coupling reactions.

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