17876-57-2

Upstream product

• 770-09-2 benzyltrimethylsilane 
• 94-36-0 dibenzoyl peroxide 
• 17903-41-2 phenyl(trimethylsilyl)methyl bromide 
• 75-77-4 chloro-trimethyl-silane 
• 108-90-7 chlorobenzene 
• 100-44-7 benzyl chloride 
• 98-87-3 benzylidene dichloride 

Downstream Products

• 131131-40-3 CH(C₆H₅)Si(CH₃)3MgCl 
• 74483-16-2 C₁₀H₁₅Cl₂PSi 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 18586-58-8 1,2-bis(trimethylsilyl)-1,2-diphenylethane 
• 81878-85-5 (S,E)-trimethyl(1-phenylbut-2-en-1-yl)silane 

Relevant academic research and scientific papers

Trimethylsilylation of carbenoids generated in situ from allyl and benzyl halides

Efficient procedures for the trimethylsilylation of the transient carbenoids H2C=CHCH(X)Li and PhCH(X)Li (X = Cl or Br) are described.

Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling

An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi-Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.

Side-chain oxidation of benzyltrimethylsilanes by iodosylbenzene in the presence of iron and manganese porphyrins

Benzyltrimethylsilanes react with iodosylbenzene in the presence of either iron(III) or magnanese(III) tetrakis(pentafluorophenyl)porphyrin (TFPPM, with M = Fe, Mn) to give α-hydroxybenzyltrimethylsilanes, which are then rapidly converted into the corresponding benzaldehydes in the reaction medium. In these reactions the active species is the metal-oxo complex. TFPPM(V) = O, formed by iodosylbenzene and TFPPM. A relative reactivity study for a series of ring substituted benzyltrimethylsilanes has shown that when M = Fe, the reaction is quite selective (ρ = -1.85), with the m-MeO substituent exhibiting a much higher reactivity than expected. When M = Mn, a lower ρ value (-1.15) is observed and no anomalous reactivity is found with the m-MeO group. These result suggest that the side-chain hydroxylation of benzyltrimethylsilane by TFPPMn(V) = O occurs by the well known hydrogen atom transfer mechanism. For the corresponding reactions induced by TFPPFe(V) = O a coupled proton/electron transfer mechanism, which might involve the formation of a charge-transfer complex, seems more likely.

Electrochemical Synthesis of (α-Halobenzyl)silanes and Benzyl Disilanes

Electrochemical reduction of a series of substituted benzal chlorides (4) in dimethylformamide containing excess chlorotrimetylsilane affords (α-chlorobenzyl)trimetylsilanes (5) or benzal (geminal) disilanes (6), depending upon experimental conditions.Benzal bromide (13) is reducted to (α-bromobenzyl)trimetylsilane (14) cleanly and in high yield without subsequent conversion to the geminal disilane 6a, apparently because of electrode passivation by bromide ion.The reaction are conveniently carried out at constant current in an undivided cell containing a stainless steel cathode and sacrificial magnesium anode.