109153-90-4

Upstream product

• 30263-03-7 3-Phenyl-3-(trimethylsilyl)-1-propanol 
• 770-09-2 benzyltrimethylsilane 
• 100-39-0 benzyl bromide 
• 94286-29-0 methyl (RS)-3-phenyl-3-trimethylsilylpropanoate 

Downstream Products

• 18586-58-8 1,2-bis(trimethylsilyl)-1,2-diphenylethane 
• 109153-93-7 3-Phenyl-3-(trimethylsilyl)propyllithium 
• 109154-06-5 C₂₄H₃₈Si₂ 

Relevant academic research and scientific papers

Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles

Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional groups. The utility of this method is demonstrated by the synthesis of pharmaceutical analogues and its use in multicomponent reactions.

Carbanion Rearrangements of ω-Phenyl-ω-(trimethylsilyl)alkyllithium Compounds: Intramolecular Reactions of Benzyltrimethylsilanes with a Carbon-Lithium Bond

ω-Phenyl-ω-(trimethylsilyl)alkyllithium compounds show four out of five theoretically conceivable possibilities for intramolecular stabilization depending on the solvent and on the chain length n.While transmetalation of a methyl group at the silicon atom by a 1,(n+2) proton transfer is observed in any case, the intramolecular 1,n shift of the benzylic proton does only take place with n >/= 4.The main reaction, however for n = 3 and 4 only, is represented by the 1,n trimethylsilyl shift via a cyclic ate complex as an intermediate which partly splits off methyllithium yielding the corresponding silacycloalkane derivatives.In going from diethyl ether to THF as the solvent, the silyl shifts are more accelerated than the proton shifts.In no case, however, a Grovenstein-Zimmermann rearrangement involving phenyl migration took place.Degenerate silyl shifts starting from α-deuterated ω-(trimethylsilyl)alkyllithium compounds could not be detected either.Only by introduction of a second trimethylsilyl group into the 3 position a 1,3-(C -> C)-trimethylsilyl shift is initiated again.