51318-07-1

Upstream product

• 109-72-8 n-butyllithium 
• 69036-00-6 1-chloro-2,2-diphenyl-1-(trimethylsilyl)ethene 
• 119-61-9 benzophenone 
• 2117-28-4 bis(trimethylsilyl)methane 
• 1068-69-5 Tris(trimethylsilyl)methane 
• 41823-71-6 bis(trimethylsilyl)methyllithium 
• 108-86-1 bromobenzene 
• 97607-44-8 1-trimethylsilyl-2-phenyl-2-trimethylstannyl-ethene 
• 2612-42-2 (dibromomethyl)trimethylsilane 
• 86997-46-8 bis(trimethylsilyl)-methyl-di-(trimethylsilyl)-methoxysilane 
• 86448-38-6 Bis-(2,4,6-trimethyl-phenyl)-trimethylsilanylmethyl-borane 
• 87161-27-1 pentamethyldisilanyldiazomethane 
• 6317-10-8 2,2-diphenyl-1,3-dithiolane 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 

Downstream Products

• 1453109-28-8 (E)-ethyl 6,6-diphenylhexa-2,5-dienoate 

Relevant academic research and scientific papers

Titanium Carbene Complexes Stabilized by Alkali Metal Amides

Facile α-H elimination from tetrakis(trimethylsilylmethyl)titanium precursors to give adducts of (alkylidene)bis(alkyl)titanium complexes is induced by light alkali metal amides of the NNNN-type macrocyclic anionic ligand Me3TACD [(Me3/su

Employing Water as the Hydride Source in Synthesis: A Case Study of Diboron Mediated Alkyne Hydroarylation

We present an approach to utilize water as the hydride source via Pd(II)/Pd(0) catalysis. As a case study, we have achieved a diboron mediated Pd(II)-catalyzed hydroarylation of alkynes using arylboronic acids. This approach not only complements conventional reactivity of Pd via Pd(0)/Pd(II) cycle for the hydroarylation but also utilizes water as the hydride source. We believe this would particularly be beneficial in utilizing water as a reagent.

Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction

Alkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, α,β-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions.

Rhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds

A rhodium-catalyzed silylation reaction of carbon - cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η2-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.

Diethylaluminum chloride mediated vinylsilane synthesis: Comparison of different solvent systems

Aromatic ketones were converted to one-carbon elongated-vinylsilanes in a convenient one-pot operation via the Peterson protocol. Reactions were conducted in two different solvents for comparison: pentane and triethylamine. Results indicate that triethylamine appeared to be a more suitable solvent for such a transformation producing vinylsilanes with great chemo- and stereo-selectivity than pentane.

Pd-catalyzed selective tandem arylation-alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

Trans -selective monoarylation of 1,1-dibromo- and 1,1-dichloro-1-alkenes (1) can be achieved in >80% yields and in ≥98-99% stereoselectivity with arylzinc bromides in the presence of a catalytic amount of Cl2Pd(DPEphos) or Cl2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of (Z)-α-bromostyrenes (3) with alkylzincs in the presence of 2 mol% of Pd(t Bu3P)2 proceeds to give the corresponding 2 in >90% yields and in ≥98-99% stereoselectivity. Although somewhat less satisfactory, the use of Cl2Pd(DPEphos) permits a one-pot tandem arylation-alkylation.

Efficient mono- and dilithiation of 2-bromo-1,1-diphenylethene with n-butyllithium/tetramethylethylenediamine

Lithiation of 2-bromo-1,1-diphenylethene (2) with n-butyllithium or tert-butyllithium/tetramethylethylenediamine (TMEDA) in pentane at -100°C effects a halogen-lithium exchange to give 2-lithio-1,1-diphenylethene (3) exclusively, which reacts with electrophiles to provide 2-substituted-1,1-diphenylethenes 5-8 in high yields. Further lithiation of the monolithium derivative 3 with n-butyllithium/TMEDA results in the direct ortho-lithiation of Z-located phenyl ring to give dilithium derivative 9, which forms disubstituted ethenes 11-13 or heterocycles 15-17 on treatment with electrophiles, tert-Butyllithium/TMEDA is ineffective for the second lithiation step.

A convenient one-pot, organoaluminum mediated vinylsilane synthesis from non-enolizable ketones via the Peterson protocol

Vinylsilanes serve as convenient vinyl anion equivalents which have gained popularity over decades. A variety of non-enolizable aromatic ketones are converted to the corresponding vinylsilanes in a one-pot procedure involving the addition of (trimethylsilylmethyl)lithium to aromatic ketones followed by addition of diethylaluminum chloride and then small amounts of water. Halide and alkoxide substituents are tolerated, and this trans-stereoselective (broad generalization; the most sterically bulky group on the double bond is trans to the trimethylsilyl group) reaction affords vinylsilanes in good yield.

Rhodium-catalyzed hydroarylation and -alkenylation of alkynes with silanediols. A crucial role of the hydroxy group for the catalytic reaction

Aryl- and alkenylsilanediols, which possess two hydroxy groups on the silicon atom, undergo the rhodium-catalyzed addition of an organic group on silicon to internal alkynes. Treatment of several internal alkynes with aryl- or alkenylsilanediols in the pr

α-Lithioalkoxysilanes: Applications to alkene synthesis

α-Lithioalkoxysilanes [RO(Me2)Si]CH(Li)(X), where R=Me or Et and X=H or SiMe3, react with carbonyl compounds in hydrocarbon solution to produce alkenes in moderate to high yield via Peterson-type reactions. For X=SiMe3, the corresponding vinylsilanes are isolated directly following work-up. The reaction is regiospecific and shows fair stereoselectivity. When the carbonyl substrates are cyclic ketones in six- or seven-membered rings, the products are exocyclic alkenes. For X=H, the initial product is a β-hydroxysilane, which is then efficiently converted to the corresponding terminal alkene by heating with sodium acetate in acetic acid. Both types of α-lithioalkoxysilane reagents are amenable to reaction with enolizable carbonyl compounds.