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907111

Sigma-Aldrich

2,6-bis(N-pyrazolyl)pyridine nickel(II) bromide

Synonym(s):

(bpp)NiBr2

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About This Item

Empirical Formula (Hill Notation):
C11H9Br2N5Ni
CAS Number:
1132833-41-0
Molecular Weight:
429.72
UNSPSC Code:
12352101
NACRES:
NA.22

form

powder or crystals

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

>300 °C

Application

Precatalyst for alkyl-alkyl cross-coupling; reductive cross-coupling of styrenyl aziridines, dialkyl ether formation, reductive amination.

Other Notes

Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination

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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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Christoph Heinz et al.
Journal of the American Chemical Society, 140(6), 2292-2300 (2018-01-18)
This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation

Related Content

Doyle Group – Professor Product Portal

Research in the Doyle group focuses on two areas: nucleophilic fluorination and nickel catalysis. The Doyle group has developed several reagents that advance these research areas. In fluorination, 2-pyridinesulfonyl fluoride (PyFluor) can be used for the mild deoxyfluorination of primary and secondary alcohols, a procedure which is normally accomplished by the sensitive reagent DAST. In nickel catalysis, the Doyle group has developed a modular, air-stable nickel precatalyst, [(TMEDA)Ni(o-tolyl)Cl], which has broad utility for a wide variety of reactions. This precatalyst can be used in place of Ni(cod)2, NiCl2, as well as other reported precatalysts. Doyle has also reported electron-deficient olefin ligands as a new class of ligand for accelerated reductive elimination. In particular, the sultam-derived ligand Fro-DO has been found to be critical for high yields in the cross-coupling of tertiary aziridines to form quaternary centers.

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