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902128

Sigma-Aldrich

(Z)-N′-Cyanopicolinimidamide

Synonym(s):

Weix 2-pyridyl-N-cyanocarboxamidine ligand for nickel catalysis

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About This Item

Empirical Formula (Hill Notation):
C7H6N4
CAS Number:
89795-81-3
Molecular Weight:
146.15
MDL number:
MFCD11227164
UNSPSC Code:
12352111

form

powder or crystals

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings
reagent type: ligand

mp

201-205 °C

SMILES string

N\C(=N\C#N)\c1ncccc1

InChI

1S/C7H6N4/c8-5-11-7(9)6-3-1-2-4-10-6/h1-4H,(H2,9,11)

InChI key

HMQYOLLIJRIQNB-UHFFFAOYSA-N

Application

This pyridyl carboxamidine ligand has been demonstrated by Daniel Weix′s lab to enable nickel-catalyzed cross-coupling of diverse basic nitrogen heterocycles with primary and secondary alkyl halides.

Other Notes

Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling

New ligands for nickel catalysis from diverse pharmaceutical heterocycle libraries

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
MKCV2506
MKCR1065
MKCQ4759
MKCP4275

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Eric C Hansen et al.
Nature chemistry, 8(12), 1126-1130 (2016-11-23)
Ligands are essential for controlling the reactivity and selectivity of reactions catalysed by transition metals. Access to large phosphine ligand libraries has become an essential tool for the application of metal-catalysed reactions industrially, but these existing libraries are not well
Eric C Hansen et al.
The Journal of organic chemistry, 82(14), 7085-7092 (2017-07-07)
Despite their importance, the synthesis of alkylated heterocycles from the cross-coupling of Lewis basic nitrogen heteroaryl halides with alkyl halides remains a challenge. We report here a general solution to this challenge enabled by a new collection of ligands based

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