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904937

Sigma-Aldrich

2,6-Bis(N-pyrazolyl)pyridine nickel (II) dichloride

≥95% anhydrous basis

Synonym(s):

(bpp)NiCl2

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About This Item

Empirical Formula (Hill Notation):
C11H9Cl2N5Ni
CAS Number:
2304667-33-0
Molecular Weight:
340.82
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

≥95% anhydrous basis

form

powder or crystals

reaction suitability

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

mp

107.9-132.4 °C (Decomp)

Related Categories

Application

2,6-Bis(N-pyrazolyl)pyridine nickel (II) dichloride ((bpp)NiCl2) is a Ni precatalyst that can be used in Negishi alkyl-alkyl cross-coupling, reductive cross-coupling of styrenyl aziridines, and dialkyl ether formation.

Other Notes

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

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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
MKCJ2564

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Brian P Woods et al.
Journal of the American Chemical Society, 139(16), 5688-5691 (2017-04-14)
A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly
Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides.
Arendt KM and Doyle AG
Angewandte Chemie (International Edition in English), 54(34), 9876-9880 (2015)
Nickel-Catalyzed Negishi Cross-Couplings of Secondary Nucleophiles with Secondary Propargylic Electrophiles at Room Temperature.
Smith SW and Fu GC
Angewandte Chemie (International ed. in English), 47(48), 9334-9336 (2008)
Nickel-catalyzed enantioselective reductive cross-coupling of styrenyl aziridines.
Woods BP, et al.
Journal of the American Chemical Society, 139(16), 5688-5691 (2017)

Articles

Nickel and Nickel-based Compounds (Complexes) as a Catalyst

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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