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901169

Sigma-Aldrich

trans-Bis(methyldiphenylphosphine)(2-methylphenyl)nickel(II) chloride

Synonym(s):

trans-(PPh2Me)2Ni(o-tolyl)Cl

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About This Item

Empirical Formula (Hill Notation):
C33H33ClNiP2
CAS Number:
1594112-89-6
Molecular Weight:
585.71
UNSPSC Code:
12352200

form

powder or solid

reaction suitability

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

mp

152-157 °C

SMILES string

Cl[Ni](PC([H])([H])[H])(P(C1=C([H])C([H])=C([H])C([H])=C1[H])(C2=C([H])C([H])=C([H])C([H])=C2[H])C([H])([H])[H])C3=C(C([H])([H])[H])C([H])=C([H])C([H])=C3[H].[H]C4=C(C5=C([H])C([H])=C([H])C([H])=C5[H])C([H])=C([H])C([H])=C4[H]

Application

The following Ni-complex is an air-stable precatalyst for various Ni-catalyzed reactions which normally require Ni(cod)2, however, this precatalyst will not require any glovebox or schlenk techniques that must be followed with Ni(cod)2. Rates are enhanced and selectivity is maintained when compared to the same reaction with Ni(cod)2.

Other Notes

Legal Information

Patent application PCT/US2014/064565. Sold under license from the Massachusetts Institute of Technology.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Recent advances in homogeneous nickel catalysis.
Tasker S Z, et al.
Nature, 509(7500), 299-299 (2014)
Sarah Z Tasker et al.
Nature, 509(7500), 299-309 (2014-05-16)
Tremendous advances have been made in nickel catalysis over the past decade. Several key properties of nickel, such as facile oxidative addition and ready access to multiple oxidation states, have allowed the development of a broad range of innovative reactions.

Articles

Jamison Nickel (II) Precatalysts

The Jamison group has developed a library of bench-stable phosphine-containing nickel(II) precatalysts that are converted into active catalysts in situ.

Nickel-based Catalysts

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

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Jamison Group – Professor Product Portal

Research in the Jamison group is centered on the development of new reactions and technologies for organic synthesis. Towards these themes, the group has pioneered a number of air-stable nickel precatalysts supported by phosphines and N-heterocyclic carbenes that are readily converted to the active catalyst in situ.

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