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804398

Sigma-Aldrich

[(TMEDA)Ni(o-tolyl)Cl]

95%

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Empirical Formula (Hill Notation):
C13H23ClN2Ni
CAS Number:
Molecular Weight:
301.48
MDL number:
PubChem Substance ID:

Quality Level

assay

95%

form

powder

reaction suitability

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

SMILES string

CC1=CC=CC=C1[Ni]Cl.CN(C)CCN(C)C

InChI

1S/C7H7.C6H16N2.ClH.Ni/c1-7-5-3-2-4-6-7;1-7(2)5-6-8(3)4;;/h2-5H,1H3;5-6H2,1-4H3;1H;/q;;;+1/p-1

InChI key

NMLMESVZRUMFAE-UHFFFAOYSA-M

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905070900941335363
[(TMEDA)Ni(o-tolyl)Cl] 95%

804398

[(TMEDA)Ni(o-tolyl)Cl]

[(TEEDA)Ni(o-tolyl)Cl] ≥95%

905070

[(TEEDA)Ni(o-tolyl)Cl]

assay

95%

assay

≥95%

assay

≥95%

assay

-

form

powder

form

powder or crystals

form

powder or solid

form

powder

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

-

Application

Effective precatalyst for a variety of nickel-catalyzed transformations, including Suzuki-Miyaura, Buchwald-Hartwig and other cyclizations and oxidative couplings.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Customers Also Viewed

Jason D Shields et al.
Organic letters, 17(9), 2166-2169 (2015-04-18)
The synthesis and catalytic activity of [(TMEDA)Ni(o-tolyl)Cl], an air-stable, crystalline solid, is described. This complex is an effective precatalyst in a variety of nickel-catalyzed transformations. The lability of TMEDA allows a wide variety of ligands to be used, including mono-

Articles

In modern transition metal-catalyzed coupling reactions, palladium has asserted its place as a dominant impetus. In comparison to previously used nickel catalysts, Pd(0) has been a proven precatalyst with diversity, accessibility, and robustness.

Related Content

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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