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917745

Sigma-Aldrich

[Ni(dtbbpy)(H2O)4]Cl2

Synonym(s):

Nickel(2+), tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]-, chloride

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About This Item

Empirical Formula (Hill Notation):
C18H32Cl2N2NiO4
CAS Number:
2035424-75-8
Molecular Weight:
470.06
MDL number:
MFCD33021751
UNSPSC Code:
12161600
NACRES:
NA.22
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form

powder

Quality Level

100

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

>300 °C

SMILES string

[Ni+2]1([NH]2=CC=C(C=C2C3=CC(=CC=[NH]31)C(C)(C)C)C(C)(C)C)(O)(O)(O)O.C

InChI key

UTKNAEDPSHMNCR-UHFFFAOYSA-J

Application

[Ni(dtbbpy)(H2O)4]Cl2 is a Ni precatalyst used in a series of Ni/photoredox dual catalysis cross-coupling reactions. These transformations include the decarboxylative coupling of oxetanyl amino acids with aryl halides.

Other Notes

Dual Photoredox/Nickel-Catalyzed Conversion of Aryl Halides to Aryl Aminooxetanes: Computational Evidence for a Substrate-Dependent Switch in Mechanism

1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis

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
MKCV3407
MKCN0073
MKCS6680

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Dual Photoredox/Nickel-Catalyzed Conversion of Aryl Halides to Aryl Aminooxetanes: Computational Evidence for a Substrate-Dependent Switch in Mechanism.
Kolahdouzan K, et al.
ACS Catalysis, 10(1), 405-411 (2020)
Álvaro Gutiérrez-Bonet et al.
ACS catalysis, 6(12), 8004-8008 (2016-12-19)
A Ni/photoredox dual catalytic cross-coupling is disclosed in which a diverse range of (hetero)aryl bromides are used as electrophiles, with 1,4-dihydropyridines serving as precursors to Csp3-centered alkyl radical coupling partners. The reported method is characterized by its extremely mild reaction

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