184095-69-0

Basic information

• Product Name: (R)-(-)-1-[(S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI(3,5-DIMETHYLPHENYL)PHOSPHINE
• Synonyms: JOSIPHOS SL-J005-1;(R,R)-1-[1-[BIS(3,5-DIMETHYLPHENYL)PHOSPHINO]ETHYL]-2-(DIPHENYLPHOSPHINO)FERROCENE;(R)-(-)-1-((S)-2-(DIPHENYLPHOSPHINO)FERROCENYL)ETHYLBIS(3,5-DIMETHYLPHENYL)PHOSPHINE;(R)-(-)-1-[(S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI(3,5-DIMETHYLPHENYL)PHOSPHINE;(R)-1-[(S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]-ETHYLDI(3,5-XYLYL)PHOSPHINE;(R)-(-)-1-[(S)-2-(Diphenylphosphino)ferrocenyl]ethyldi-3,5-xylylphosphine,min.97%;(r,r)-1-{1-[bis(3,5-dimethylphenyl)phosphino]ethyl}-2-(diphenylphosphino)ferrocene (acc to cas);(R)-(-)-1-[(S)-2-(DIPHENYLPHOSPHINO) FERROCENYL]ETHYLDI-3,5-XYLYLPHOSPHINE, MIN. 97%
• CAS NO: 184095-69-0
• Molecular Formula: C40H40FeP2 10*
• Molecular Weight: 638.54
• Product Categories: organophosphine ligand;Chiral Phosphine;Ferrocene Series;Josiphos Series
• Mol File: 184095-69-0.mol
• Article Data: 2

Chemical Properties

• Appearance: orange/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (R)-(-)-1-[(S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI(3,5-DIMETHYLPHENYL)PHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-[(S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI(3,5-DIMETHYLPHENYL)PHOSPHINE(184095-69-0)
• EPA Substance Registry System: (R)-(-)-1-[(S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI(3,5-DIMETHYLPHENYL)PHOSPHINE(184095-69-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 184095-69-0(Hazardous Substances Data)

Usage

Reactions

Ligand for Rhodium-catalyzed asymmetric hydrogenation in the synthesis of tertiary carbinamide.

Chemical Properties

Orange powder

General Description

sold in collaboration with Solvias AG

InChI:InChI=1/C35H35P2.C5H5.Fe/c1-25-19-26(2)22-32(21-25)36(33-23-27(3)20-28(4)24-33)29(5)34-17-12-18-35(34)37(30-13-8-6-9-14-30)31-15-10-7-11-16-31;1-2-4-5-3-1;/h6-24,29H,1-5H3;1-5H;/t29-;;/m0../s1

Upstream product

• 12098-17-8 (diphenylphosphin)ferrocene 

Relevant articles and documents

Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination

Herein we report the copper-catalyzed silylation of propargylic difluorides to generate axially chiral, tetrasubstituted monofluoroallenes in both good yields (27 examples >80%) and enantioselectivities (82-98% ee). Compared to previously reported synthetic routes to axially chiral allenes (ACAs) from prochiral substrates, a mechanistically distinct reaction has been developed: the enantiodiscrimination between enantiotopic fluorides to set an axial stereocenter. DFT calculations and vibrational circular dichroism (VCD) suggest that β-fluoride elimination from an alkenyl copper intermediate likely proceeds through a syn-β-fluoride elimination pathway rather than an anti-elimination pathway. The effects of the C1-symmetric Josiphos-derived ligand on reactivity and enantioselectivity were investigated. Not only does this report showcase that alkenyl copper species (like their alkyl counterparts) can undergo β-fluoride elimination, but this elimination can be achieved in an enantioselective fashion.