19960-77-1

Upstream product

• 109-72-8 n-butyllithium 
• 766-77-8 Dimethylphenylsilane 
• 694-53-1 phenylsilane 
• 917-54-4 methyllithium 
• 768-33-2 phenyldimethylsilyl chloride 
• 1119-90-0 di-n-butylzinc 
• 33668-60-9 iodo(dimethyl)(phenyl)silane 
• 92273-73-9 n-butylzinc bromide 
• 542-69-8 1-iodo-butane 
• 102-67-0 tri-n-propylaluminum 
• 71864-24-9 (chlorolithiomethyl)dimethylphenylsilane 
• 107-00-6 but-1-yne 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1833-51-8 chloromethyldimethylphenylsilane 

Downstream Products

• 32328-67-9 1-phenyl-4-(chlorodimethylsilyl)-butane 

Relevant academic research and scientific papers

Continuous-flow Si-H functionalizations of hydrosilanesviasequential organolithium reactions catalyzed by potassiumtert-butoxide

We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanesviaserial organolithium reactions catalyzed by earth-abundant metal compounds. Based on the screening of various additives, we found that catalytic potassiumtert-butoxide (t-BuOK) facilitates the rapid reaction of organolithiums with hydrosilanes. Using a flow microreactor system, various organolithiums bearing functional groups were efficiently generatedin situunder mild conditions and consecutively reacted with hydrosilanes in the presence oft-BuOK within 1 min. We also successfully conducted the di-funtionalizations of dihydrosilane by sequential organolithium reactions, extending to a gram-scale-synthesis. Finally, the combinatorial functionalizations of trihydrosilane were achieved to give every conceivable combination of tetrasubstituted organosilane libraries based on a precise reaction control using an integrated one-flow system.

Thermal, Catalytic Conversion of Alkanes to Linear Aldehydes and Linear Amines

Alkanes, the main constituents of petroleum, are attractive feedstocks for producing value-added chemicals. Linear aldehydes and amines are two of the most important building blocks in the chemical industry. To date, there have been no effective methods for directly converting n-alkanes to linear aldehydes and linear amines. Here, we report a molecular dual-catalyst system for production of linear aldehydes via regioselective carbonylation of n-alkanes. The system is comprised of a pincer iridium catalyst for transfer-dehydrogenation of the alkane using t-butylethylene or ethylene as a hydrogen acceptor working sequentially with a rhodium catalyst for olefin isomerization-hydroformylation with syngas. The system exhibits high regioselectivity for linear aldehydes and gives high catalytic turnover numbers when using ethylene as the acceptor. In addition, the direct conversion of light alkanes, n-pentane and n-hexane, to siloxy-terminated alkyl aldehydes through a sequence of Ir/Fe-catalyzed alkane silylation and Ir/Rh-catalyzed alkane carbonylation, is described. Finally, the Ir/Rh dual-catalyst strategy has been successfully applied to regioselective alkane aminomethylation to form linear alkyl amines.

METHOD FOR PREPARING SILAHYDROCARBONS

The present disclosure is directed to a process for preparing silahydrocarbons of formula (I), the process comprising the step of reacting a compound of formula (II), with a compound of formula (III), as well as to silahydrocarbons prepared by such a process, and to compositions and articles of manufacture comprising such silahydrocarbons.

Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction

We report the first example of a silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles. This palladium-catalyzed process provides direct access to alkyl silanes. The delicate balance of steric and electronic parameters of the employed DrewPhos ligand is paramount to suppressing isomerization and promoting efficient and selective cross-coupling.

Palladium-Catalyzed Cross-Coupling of Monochlorosilanes and Grignard Reagents

Using a palladium catalyst supported by DrewPhos, the alkylation of monochlorosilanes with primary and secondary alkylmagnesium halides is now possible. Arylation with sterically demanding aromatic magnesium halides is also enabled. This transformation ov

Direct synthesis of alkylsilanes by platinum-catalyzed coupling of hydrosilanes and iodoalkanes

Alkyl iodides and tertiary silanes were successfully coupled with good functional group tolerance using a Pt(P(tBu)3)2/(iPr) 2EtN/CH3CN system. The utility of the methodology is demonstrated by the synthesis of silafluofen, a Si-containing insecticide. This journal is The Royal Society of Chemistry.

The stereochemistry of the vinylogous Peterson elimination

Base-induced eliminations of the vinylogous β-hydroxysilanes 7, 9, 11 and 12 are stereospecifically syn, giving largely the trans,trans-diene 8 from 7 and 11, the cis,trans-diene 10 from 9, and the trans,cis-diene 13 from 12. When a cis double bond is produced, it is selectively placed adjacent to the carbon atom that originally carried the hydroxy group. E2′ Reactions with silyl as the electrofugal group and acetate as the nucleofugal group, initiated by fluoride ion, are not stereospecific, but can be highly stereoselective in favour of the trans,trans-diene 8 when the carbon substituent at the silicon-bearing end is a cyclohexyl group and the double bond is cis, and in favour of the trans,cis-diene 13 when the carbon substituent at the silicon-bearing end is a methyl group and the double bond is trans. Attempts to use the Peterson reactions to make o-quinodimethanes stereospecifically failed, with no evidence of 1,4-elimination from the alcohols 40 and 41. The corresponding E2′ reaction from the esters using fluoride ion on the acetates or formates 46 and 47 gave stereoselectively the E,E-quinodimethane 48.