13360-20-8

Upstream product

• 766-77-8 Dimethylphenylsilane 
• 107-18-6 allyl alcohol 
• 59413-34-2 potassium (phenyl)dimethylsilanololate 
• 7646-75-5 sodium phenyldimethylsilanolate 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 80735-94-0 1-Phenyl-3-buten-1-ol 

Relevant academic research and scientific papers

Reduction of allylpalladium(II)chloride dimer by formation of allyloxysilanes

The reduction of allylpalladium(II)chloride dimer (APC) to a Pd(0) species can be effected by reaction with alkali metal silanolates. The reduction is extremely rapid in the presence of chelating bisphosphine ligands and for a variety of silanolates. Geor

An efficient solvent-free route to silyl esters and silyl ethers

Dinuclear metal complexes, especially (p-cymene)ruthenium dichloride dimer {[RuCl2(p-cymene)]2}, have been found to exhibit high catalytic performance for the dehydrosilylation of various kinds of carboxylic acids and alcohols. The dehydrosilylation with [RuCl2(p-cymene)] 2 proceeded efficiently with only one equivalent of silane with respect to substrate (carboxylic acids or alcohols) under solvent-free conditions to give the corresponding silyl esters and ethers in excellent yields with a high turnover number (TON) and frequency (TOF). The 1H NMR spectrum of a toluene-d8 solution of [RuCl2(p-cymene)] 2 and a silane showed a signal assignable to the ruthenium hydride species. In contrast, no new signals were detected in the 1H NMR spectrum of a toluene-d8 solution of [RuCl2(p-cymene)] 2 and a carboxylic acid or an alcohol. There-fore, the ruthenium metal in [RuCl2(p-cymene)]2 activates a silane to afford the hydride intermediate, possibly a silylmetal hydride species. Then, the nucleophilic attack of a substrate (carboxylic acid or alcohol) to the hydride intermediate proceeds to give the corresponding silylated product. The present dehydrosilylation with an optically active silane proceeded exclusively under inversion of stereochemistry at the chiral silicon center, suggesting that the nucleophilic attack of a substrate to the hydride intermediate occurs from the backside of the ruthenium-silicon bond.

An Efficient Catalyst for the Conversion of Hydrosilanes to Alkoxysilanes

The copper(I) hydride 6 is an efficient catalyst for the alcoholysis of primary and secondary silanes.The reactions proceed at room temperature within a few hours and give the alkoxysilanes in high yields.Only with bulky alcohols or silanes are longer reaction times and/or increased temperatures required.The presence of air accelarates the reactions and gives rise to higher yields of alkoxysilanes, particularly with bulky alcohols.Diols react with PhRSiH2 (R = Me, Ph) to afford 1,3-dioxo-2-silacycloalkanes and with tertiary silanes to furnish the bissilylated diols.When unsaturated alcohols (2-propen-1-ol or 2-propyn-1-ol) are employed, the double or triple bond is retained. - Keywords: Catalytic silane alcoholysis; Alkoxysilanes

Direct Transformation of Allylic and Benzylic Alcohols or Their Silylated Derivatives into Orgnolithium Compounds

The reaction of allylic or benzylic alcohols 1 with n-butyllithium followed by treatment with lithium powder and a catalytic amount of DTBB (5 mol percent) in THF at room temperature gives a solution of the corresponding alkyllithium reagent, which reacts in situ with different electrophiles to yield the expected products 2.Alternatively, the O-silylated derivatives of the same alcohols are lithiated under Barbier-type reaction conditions to afford the same reaction products with better yields.