903000
[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride
powder or crystals
Synonym(s):
(4,4′-dtbbpy)NiCl2
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About This Item
Empirical Formula (Hill Notation):
C18H24Cl2N2Ni
CAS Number:
Molecular Weight:
398.00
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
Product Name
[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride,
InChI key
PCWIKFRTCXESOT-UHFFFAOYSA-L
SMILES string
CC(C1=CC(C2=CC(C(C)(C)C)=CC=N2)=NC=C1)(C)C.Cl[Ni]Cl
form
powder or crystals
reaction suitability
core: nickel
reaction type: Cross Couplings
reagent type: catalyst
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
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)
Lingling Chu et al.
Angewandte Chemie (International ed. in English), 54(27), 7929-7933 (2015-05-28)
The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate
Wacharee Harnying et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(17), 4765-4773 (2011-03-23)
The roles of nickel and chromium catalysts in the coupling reaction of vinyl halides and aldehydes, the so-called Nozaki-Hiyama-Kishi (NHK) reaction, have been studied by UV/Vis spectroscopy, electrochemical, and spectroelectrochemical methods. Electrochemical studies revealed that nickel plays the central role
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)
Articles
Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.
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