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900941

Sigma-Aldrich

Chloro(4-cyanophenyl)[(R)-1-[(S)-2-[bis(4-fluorophenyl]phosphino]ferrocenyl]ethyldi-tert-butylphosphine]nickel(II)

≥95%

Synonym(s):

SK-J014-1n

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About This Item

Empirical Formula (Hill Notation):
C39H42ClF2FeNNiP2
CAS Number:
2049086-37-3
Molecular Weight:
774.69
UNSPSC Code:
12352103
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder or solid

reaction suitability

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

SMILES string

CC(C)(C)P(C(C)(C)C)C[C]1[C][C][C][C]1P(C2=CC=C(F)C=C2)C3=CC=C(F)C=C3.Cl[Ni]C4=CC=C(C#N)C=C4.[C]5[C][C][C][C]5.[Fe]

Application

Amination of functionalized aryl chlorides with ammonia and ammonium salts.

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)

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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)
Ni?Catalyzed Amination Reactions: An Overview.
Marin M, et al.
Chemical Record, 16(4), 1819-1832 (2016)
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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