158923-11-6

Basic information

• Product Name: (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE
• Synonyms: (R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyli-tert-butylphosphine;(R)-(S)-cy2PF-PtBu2;(R)-1-[(SP)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine;(R)-1-[(SP)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine >=97%;(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene,1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-,(2R)-;JOSIPHOS SL-J009-1;(R,R)-1-[1-(DI-TERT-BUTYLPHOSPHINO)ETHYL]-2-(DICYCLOHEXYLPHOSPHINO)FERROCENE
• CAS NO: 158923-11-6
• Molecular Formula: C₃₂H₅₂FeP₂
• Molecular Weight: 554.55
• Product Categories: organophosphine ligand;Chiral Phosphine;Ferrocene Series;Josiphos Series
• Mol File: 158923-11-6.mol
• Article Data: 1

Chemical Properties

• Appearance: orange/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Very Slightly)
• CAS DataBase Reference: (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE(158923-11-6)
• EPA Substance Registry System: (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE(158923-11-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 158923-11-6(Hazardous Substances Data)

Usage

Reaction

Ligand for Palladium-catalyzed C-N cross-coupling. Ligand for Palladium-catalyzed C-S cross-coupling. Ligand for Palladium-catalyzed Kumada couplings of aryl and vinyl tosylates. Ligand for Rhodium-catalyzed hydroacylation of cyclopropenes, an enatioselective desymmetrization method. Ligand for Palladium-catalyzed C-O cross-coupling. Ligand for Rhodium-catalyzed coupling of imidazole derivatives with terminal allenes. Ligand for Ruthenium-catalyzed C-C coupling of alkynes and alcohols to form branched products of carbonyl allylation

Chemical Properties

Orange powder

Uses

It may be used as a ligand in the palladium catalyzed hetero cross-coupling between aryl bromides/aryl triflates with potassium thioacetate to form S-aryl thioacetates.

General Description

sold in collaboration with Solvias AG

InChI:InChI=1/C27H47P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h14,19-23H,8-13,15-18H2,1-7H3;1-5H;/t21-;;/m0../s1

Downstream Products

• 1154042-92-8 [Pd(1-dicyclohexylphosphino-2-di-tert-butylphosphinoethylferrocene)(H)(2-propanethiolate)] 
• 1154042-81-5 [Pd(1-dicyclohexylphosphino-2-di-tert-butylphosphinoethylferrocene)(p-tolyl)Br] 
• 583872-37-1 [Pd(1-dicyclohexylphosphino-2-di-tert-butylphosphinoethylferrocene)(P(o-tolyl)3)] 
• 942627-96-5 (C₅H₅)Fe(C₅H₃(CH(CH₃)P(C(CH₃)3)2)P(C₆H₁₁)2)PtCl₂ 

Relevant articles and documents

Synthesis of ferrocenyl diphosphine ligands: Substitution of α-methoxy or α-dimethylamino groups by phosphines. Retention versus inversion: A stereochemical study

The stereochemical course of the exchange reaction of α-methoxy or α-dimethylamino groups by phosphines in acetic acid has been studied for ferrocene derivatives that have either a ferrocenylethyl or a benzylferrocenyl backbone. The reaction proceeded with either retention or inversion of configuration depending on the substrate stereoisomer used. The parameters that influence the stereochemical course of these reactions, such as relative configuration or substitution patterns, are discussed.