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901166

Sigma-Aldrich

cis-[2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl](2-methylphenyl)nickel(II) chloride

Synonym(s):

cis-((S)-BINAP)Ni(o-tolyl)Cl

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About This Item

Empirical Formula (Hill Notation):
C51H39ClNiP2
CAS Number:
1594113-05-9
Molecular Weight:
807.95
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder or solid

Quality Level

100

reaction suitability

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

mp

>300 °C

SMILES string

Cl[Ni]1(P(C2=C([H])C([H])=C([H])C([H])=C2[H])(C3=C([H])C([H])=C([H])C([H])=C3[H])C(C([H])=C4[H])=[C@@]([C@@]5=C(P1(C6=C([H])C([H])=C([H])C([H])=C6[H])C7=C([H])C([H])=C([H])C([H])=C7[H])C([H])=C([H])C8=C5C([H])=C([H])C([H])=C8[H])C9=C4C([H])=C([H])C([H])=C

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.

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF3673

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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 and Nickel-based Compounds (Complexes) as a Catalyst

Nickel transition metal and its complexes can be used as a catalyst in many synthetic transformations, like oxidative addition, C-H activation, reductive elimination, oxidative cyclization, oligomerization, and in cross-coupling reactions.

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