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900943

Sigma-Aldrich

Chloro(4-cyanophenyl)[(R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine]nickel(II)

Synonym(s):

SK-J003-1n

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About This Item

Empirical Formula (Hill Notation):
C43H60ClFeNNiP2
CAS Number:
2049086-35-1
Molecular Weight:
802.88
UNSPSC Code:
12352103
NACRES:
NA.22

form

powder or solid

Quality Level

100

reaction suitability

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

SMILES string

Cl[Ni+2]C1=CC=C(C#N)C=C1.C[C@@H](P(C2CCCCC2)C3CCCCC3)[C]4[C][C][C][C]4P(C5CCCCC5)C6CCCCC6.[C]7[C][C][C][C]7.[Fe]

Application

Amination of aryl chlorides, bromides and sulfonates with ammonia. Amination of aryl carbamates with ammonia or ammonium salts.

Other Notes

Nickel-Catalyzed Monoarylation of Ammonia
Valorization of the Primary Building Blocks Ammonia and Acetone Featuring Pd- and Ni-Catalyzed Monoarylations

Signal Word

Warning

Hazard Statements

H315,H361d,H411

Hazard Classifications

Aquatic Chronic 2 - Repr. 2 - Skin Irrit. 2

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ni?Catalyzed Amination Reactions: An Overview.
Marin M, et al.
Chemical Record, 16(4), 1819-1832 (2016)
Nickel?Catalyzed Amination of Aryl Chlorides with Ammonia or Ammonium Salts.
Green R A and Hartwig J F
Angewandte Chemie (International Edition in English), 54(12), 3768-3772 (2015)
Evaluating 1, 1?-Bis (phosphino) ferrocene Ancillary Ligand Variants in the Nickel-Catalyzed C?N Cross-Coupling of (Hetero) aryl Chlorides.
Clark J S, et al.
Organometallics, 36(3), 679-686 (2017)
Nickel?Catalyzed Monoarylation of Ammonia.
Borzenko A, et al.
Angewandte Chemie (International Edition in English), 54(12), 3773-3777 (2015)
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.

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