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902039

Sigma-Aldrich

4-Methoxypicolinimidamide hydrochloride

≥95%

Synonym(s):

Weix 2-pyridylcarboxamidine ligand for nickel catalysis

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About This Item

Empirical Formula (Hill Notation):
C7H10ClN3O
CAS Number:
1179361-66-0
Molecular Weight:
187.63
MDL number:
MFCD12755550
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

≥95%

form

powder or solid

reaction suitability

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

mp

174-176 °C

SMILES string

Cl.N\C(=N/[H])\c1nccc(c1)OC

InChI

1S/C7H9N3O.ClH/c1-11-5-2-3-10-6(4-5)7(8)9;/h2-4H,1H3,(H3,8,9);1H

InChI key

JOUDWIBACXLPIO-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
Electrochemical Nickel Catalysis for Sp2-Sp3 Cross-Electrophile Coupling Reactions of Unactivated Alkyl Halides

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Robert J Perkins et al.
Organic letters, 19(14), 3755-3758 (2017-07-14)
A constant-current electrochemical method for reducing catalytic nickel complexes in sp2-sp3 cross-electrophile coupling reactions has been developed. The electrochemical reduction provides reliable nickel catalyst activation and turnover and offers a tunable parameter for reaction optimization, in contrast to more standard
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
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

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