13272-89-4

Basic information

• Product Name: Silane, bis(4-fluorophenyl)-
• CAS NO: 13272-89-4
• Molecular Formula: C12H10F2Si
• Molecular Weight: 220.294
• Mol File: 13272-89-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Silane, bis(4-fluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, bis(4-fluorophenyl)-(13272-89-4)
• EPA Substance Registry System: Silane, bis(4-fluorophenyl)-(13272-89-4)

Safety Data

• Hazardous Substances Data: 13272-89-4(Hazardous Substances Data)

Upstream product

• 33715-54-7 C₁₆H₁₈F₂O₂Si 
• 13272-84-9 (4-fluorophenyl)silane 
• 2339-43-7 bis(4-fluorophenyl)dichlorosilane 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 13272-82-7 Bis-<4-fluor-phenyl>-chlor-silan 

Downstream Products

• 221649-90-7 cis-Pt(SiHC₆H₄F-p)2(PEt₃)2 
• 219789-59-0 mer-[RhH(SC₆H₄OMe-p)(SiH(C₆H₄F-p)2)(PMe₃)3] 
• 194282-02-5 mer-RhCl(H)[SiH(C₆H₄F-p)2] 
• 192313-14-7 RhH(SiH(C₆H₄-p-F)2)(SC₆H₄-p-Me)(PMe₃)3 

Relevant articles and documents

Gold(I) complexes with chloro(diaryl)silyl ligand. Stoichiometric reactions and catalysis for O-functionalization of organosilane

An Au(I) complex with a chloro(diphenyl)silyl ligand [Au(SiPh2Cl)(PCy3)] (1a) is obtained from the reaction of Ph2SiH2 with [AuCl(PCy3)]. (4-FC6H4)2SiH2, (4-MeC6H4)2SiH2, and Ph2GeH2 react with [AuCl(PCy3)] to form complexes with the chlorodiarylsilyl ligand, [Au(SiAr2Cl)(PCy3)] (1b: Ar = C6H4-4-F, 1c: Ar = C6H4-4-Me) and with the chloro(diphenyl)germyl ligand, [Au(GePh2Cl)(PCy3)] (2a), respectively. Complex 1a reacts with H2O to form Ph2SiH(OH) and (Ph2SiH)2O, whereas the reaction of EtOH with 1a yields Ph2SiH(OEt) exclusively. Complex 1a catalyzes the hydrolysis of Ph2SiH2 ([Au]:[H2SiPh2]:[H2O] = 0.05:1.0:10.0) at 60 °C to yield Ph2SiH(OH) and (Ph2SiH)2O. The reaction of Ph2SiH2 with HOEt in the presence of a catalytic amount of 1a affords Ph2SiH(OEt). Both stoichiometric and catalytic reactions using 1a lead to the recovery of [AuCl(PCy3)] from the reaction mixture.

Divalent Ytterbium Complex-Catalyzed Homo- and Cross-Coupling of Primary Arylsilanes

Redistribution of primary silanes through C-Si and Si-H bond cleavage and reformation provides a straightforward synthesis of secondary silanes, but the poor selectivity and low efficiency severely hinders the application of this synthetic protocol. Here, we show that a newly synthesized divalent ytterbium alkyl complex exhibits unprecedentedly high catalytic activity toward the selective redistribution of primary arylsilanes to secondary arylsilanes. More significantly, this complex also effectively catalyzes the cross-coupling between electron-withdrawing substituted primary arylsilanes and electron-donating substituted primary arylsilanes to secondary arylsilanes containing two different aryls. DFT calculation indicates that the reaction always involve the exothermic formation of a hypervalent silicon upon facile addition of PhSiH3 to the Yb-E (E = C, H) bond. This hypervalent compound can easily either generate directly the Yb-Ph complex, or indirectly through the formation of Yb-H, that is the key complex for the formation of Ph2SiH2.

Dichotomy of Manganese Catalysis via Organometallic or Radical Mechanism: Stereodivergent Hydrosilylation of Alkynes

Herein, we disclose the first manganese-catalyzed hydrosilylation of alkynes featuring diverse selectivities. The highly selective formation of E-products was achieved by using mononuclear MnBr(CO)5 with the arsenic ligand, AsPh3. Whereas using the dinuclear catalyst Mn2(CO)10 and LPO (dilauroyl peroxide) enabled the reversed generation of Z-products in good to excellent stereo- and regioselectivity. Such a way of controlling the reaction stereoselectivity is unprecedented. Mechanistic experiments revealed the dichotomy of manganese catalysis via organometallic and radical pathways operating in the E- and Z-selective routes, respectively.