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804398

Sigma-Aldrich

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

95%

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About This Item

Empirical Formula (Hill Notation):
C13H23ClN2Ni
CAS Number:
1702744-45-3
Molecular Weight:
301.48
MDL number:
MFCD29037017
UNSPSC Code:
12161600
PubChem Substance ID:
329768866
NACRES:
NA.22

Quality Level

100

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

Related Categories

Application

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

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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
SHBL0528
MKBX0364V
MKBW0792V

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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

Broad Application Doyle Nickel Precatalyst

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

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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