144789-20-8

Upstream product

• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 300-57-2 allylbenzene 
• 14371-10-9 (E)-3-phenylpropenal 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 24808-74-0 (E)-(3-methoxybut-1-en-1-yl)benzene 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 
• 74-88-4 methyl iodide 
• 917-54-4 methyllithium 
• 31930-44-6 trans-1-phenyl-3-trimethylsilyl-2-propen-1-ol 

Downstream Products

• 83972-44-5 1-phenyl-3-(trimethylsilyl)butane 

Relevant academic research and scientific papers

Attenuation of Ni(0) Decomposition: Mechanistic Insights into AgF-Assisted Nickel-Mediated Silylation

In nickel-mediated Kumada cross-coupling reactions, low valent active nickel complexes are often generated in situ and the ligands usually govern the reactivity or stability of these complexes. However, the decomposition of active nickel complexes is inev

Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage

Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.

Silylation of Allylic Trifluoroacetates and Acetates Using Organodisilanes Catalyzed by Palladium Complex

Silylation of allylic acetates (1) using organodisilanes (2) was carried out in the presence of a catalytic amount of Pd(DBA)2-LiCl at 100 deg C. The silylation proceeded smoothly without β-hydrogen elimination of a resulting (?-allyl)palladium intermediate. The added chloride salt such as LiCl or NaCl was indispensable for the catalytic activity. On the other hand, remarkable improvement of the silylation was realized by employing allylic trifluoroacetates (4) in place of the acetates (1) as the substrates. The silylation proceeded even at room temperature, and the added chloride salts was not necessary as the catalyst component. In the silylation, transmetalation of the disilanes (2) with (η3-allyl)palladium intermediate (7) might be a critical step in the catalytic cycle. Model reactions for the transmetalation were carried out.

Chiral organosilicon compounds in synthesis. Preparation and stereoselective alkylations of silylcinnamyl carbanions

Silylallyl carbanions of type 13 bearing a chiral lithium complexing substituent remote from silicon can be alkylated regio- and stereoselectively at the α-position by small electrophiles in nonpolar solvents.The regiochemical outcome of the reaction was found to be highly dependent on the size of the incoming electrophile.Secondary alkyl halides react preferentially at the γ-center and good levels of stereoselectivity are still obtained in nonpolar solvents despite the rather long distance between the reacting center and the chiral auxiliary.Transformation of the alkylated allylsilanes into optically active alcohols and carboxylic acids may represent a potential synthetic application of the method.

REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALLYLSILANES USING (METHYLPHENYLAMINO)TRIBUTYLPHOSPHONIUM IODIDE

Regio- and stereoselective synthesis of variously substituted allylsilanes is achieved by organocuprate-mediated γ-coupling of allylic alcohols using the title reagent (1).