187344-98-5

Basic information

• Product Name: BIS(3,5-BIS(TRIMETHYLSILYL)PHENYL)PHOSPHINE OXIDE
• Synonyms: BIS(3,5-BIS(TRIMETHYLSILYL)PHENYL)PHOSPHINE OXIDE
• CAS NO: 187344-98-5
• Molecular Formula: C₂₄H₄₃OPSi₄
• Molecular Weight: 490.91
• Mol File: 187344-98-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BIS(3,5-BIS(TRIMETHYLSILYL)PHENYL)PHOSPHINE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(3,5-BIS(TRIMETHYLSILYL)PHENYL)PHOSPHINE OXIDE(187344-98-5)
• EPA Substance Registry System: BIS(3,5-BIS(TRIMETHYLSILYL)PHENYL)PHOSPHINE OXIDE(187344-98-5)

Safety Data

• Hazardous Substances Data: 187344-98-5(Hazardous Substances Data)

Upstream product

• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 159418-75-4 bis[3,5-bis(trimethylsilyl)phenyl]chlorophosphine 

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.