ChemicalBook Product Catalog Chemical Reagents Organic reagents Phosphine ligand (R)-(-)-1-[(S)-2-(DI(3,5-BIS-TRIFLUOROMETHYLPHENYL)PHOSPHINO)FERROCENYL]ETHYLDICYCLOHEXYLPHOSPHINE

(R)-(-)-1-[(S)-2-(DI(3,5-BIS-TRIFLUOROMETHYLPHENYL)PHOSPHINO)FERROCENYL]ETHYLDICYCLOHEXYLPHOSPHINE

Product Name(R)-(-)-1-[(S)-2-(DI(3,5-BIS-TRIFLUOROMETHYLPHENYL)PHOSPHINO)FERROCENYL]ETHYLDICYCLOHEXYLPHOSPHINE
CAS292638-88-1
MFC40H40F12FeP210*
MW866.52
EINECS
MOL File292638-88-1.mol

Chemical Properties

alpha	-260° ±15° (c 0.5, CHCl3)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
form	Powder
color	orange
InChIKey	QRWXESUNHGCSDF-GHVWMZMZSA-N
SMILES	[Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][C]2P(c3cc(cc(c3)C(F)(F)F)C(F)(F)F)c4cc(cc(c4)C(F)(F)F)C(F)(F)F)P(C5CCCCC5)C6CCCCC6
CAS DataBase Reference	292638-88-1

Safety Information

WGK Germany	3
HS Code	29319090
Storage Class	13 - Non Combustible Solids

Usage And Synthesis

Reaction

Ferrocenylphosphine ligands of the type cpFecp(PR2)(*CH(CH3)PR'2) are a class of asymmetric ligands developed at Solvias in Basel, Switzerland. Ligands of this type are currently used industrially in the stereoselective synthesis of commercial products2,3. A unique feature of these bidentate ligands is the presence of a fixed phosphine moiety and a stereogenic, functionalized side chain, which can be easily modified to accommodate electronic and steric requirements. Based on a versatile synthetic procedure starting with optically active ferrocenes of the type cpFecp(PR2)(*CH(CH3)X) [X = OAc or NR2], a variety of donor atoms can be introduced into the side chain.4 These ferrocene based phosphine ligands have wide application in the stereoselective hydrogenation of substituted acetamidoacrylates, enol acetates, β-ketoesters and simple alkenes.
Useful as a ligand in Pd-catalyzed C-N bond-forming reactions.
Pd-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides.
Asymmetric hydrogenation of ketones and phosphinylketimines.
Michael addition of Grignard reagents to α,α-unsaturated esters and thioesters.
Boration of ∀,∃-unsaturated esters and nitriles.
Reaction of aryl halides with ammonia.
Cu-catalyzed reduction of activated C=C bonds with PMHS.
Regio- and enantioselective hydroboration of vinyl arenes.
Rh-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes.
1,2-Migrations in Pd-catalyzed Negishi couplings with JosiPhos ligands.
Catalyst for the homodimerization of ketoketenes.
Ligand for the Rh catalyzed synthesis of lactones.
Ligand for the Cu-catalyzed synthesis of syn and anti γ-amino alcohols.

Chemical Properties

Orange powder

General Description

sold in collaboration with Solvias AG

(R)-(-)-1-[(S)-2-(DI(3,5-BIS-TRIFLUOROMETHYLPHENYL)PHOSPHINO)FERROCENYL]ETHYLDICYCLOHEXYLPHOSPHINE Supplier

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