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903000

Sigma-Aldrich

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

Synonym(s):

(4,4′-dtbbpy)NiCl2

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About This Item

Empirical Formula (Hill Notation):
C18H24Cl2N2Ni
CAS Number:
1034901-50-2
Molecular Weight:
398.00
MDL number:
MFCD31807325
UNSPSC Code:
12352101
NACRES:
NA.22

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

InChI key

PCWIKFRTCXESOT-UHFFFAOYSA-L

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.

Other Notes

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

Photocatalytic α-Acylation of Ethers

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN3311
SHBL5154
MKCH6491

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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
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)
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