60565-09-5

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 1728-18-3 dimethylacetal of cyclohexenone 
• 930-68-7 cyclohexenone 
• 98-86-2 acetophenone 
• 1170695-27-8 C₁₃H₂₂OSi₂ 
• 64340-80-3 Dimethyl-(1-phenyl-vinyloxy)-silane 
• 17851-98-8 1-phenyl-1-(tributylstannyloxy)ethene 
• 81555-46-6 (Z)-2-Benzoyl-octa-2,7-dienoic acid ethyl ester 
• 4747-13-1 α-methoxystyrene 
• 13735-78-9 1-phenyl-2-(trimethylsilyl)ethanone 

Relevant academic research and scientific papers

Lewis Acid Catalysis with Cationic Dinuclear Gold(II,II) and Gold(III,III) Phosphorus Ylide Complexes

The dinuclear gold(II,II) and gold(III,III) complexes [Au2(μ-PY)2(MeCN)2]OTf2 (2-OTf2) and [Au2(μ-PY)2(μ-CH2)(MeCN)2]OTf2 (3-OTf2) (PY = [(CH2)2PPh2]-) have been synthesized and evaluated as Lewis acid catalysts for Mukaiyama addition and alkyne hydroamination reactions. 2-OTf2 and 3-OTf2 provide similar or improved catalytic activity for these reactions compared to the commonly used gold(I) Lewis acids Ph3PAuOTf and IPrAuOTf. The versatile Lewis acidity of 2-OTf2 was further demonstrated by its superior performance in a cascade reaction involving intramolecular hydroamination followed by intermolecular conjugate addition to generate a 2,3-substituted indole.

Synthesis and structures of air-stable binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate and their catalytic application in C-C bond-forming reactions

The two air-stable m2-hydroxy-bridged binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate complexes were successfully synthesized. The high catalytic activity and recyclability of these complexes were exemplified for various carbon-carbon bond formation reactions. Compared with our previously reported hafnocene perfluorooctanesulfonate, these complexes show stronger Lewis acidity and better catalytic activity, and should find broad applications in organic synthesis.

Development of N,N-bis(perfluoroalkanesulfonyl)squaramides as new strong Br?nsted acids and their application to organic reactions

New strong Br?nsted acids derived from a squaric acid scaffold bearing different perfluoroalkanesulfonyl groups have been developed and applied to several organic reactions. These squaramides are bench-stable and exhibit much higher reactivities in several organic reactions than squaric acid itself. N,N-Bis(trifluoromethanesulfonyl)squaramide 2a was applied to the Mukaiyama aldol reaction and Mukaiyama Michael reaction. Mechanistic studies revealed that the Br?nsted acid might be the predominant catalyst through direct protonation of carbonyl compound by the acid itself rather than the silylated Br?nsted acid. The utility of this acid 2a was further extended to Hosomi-Sakurai allylation of aldehydes and a carbonyl-ene reaction. Furthermore, other squaramides 2b and c bearing longer perfluoroalkyl chains have been developed, which are also bench-stable and displayed similar reactivities with squaramide 2a in several organic reactions.

A new Br?nsted acid derived from squaric acid and its application to Mukaiyama aldol and Michael reactions

Bis-N-trifluoromethanesulfonyl squaramide was prepared as a new bench-stable strong Br?nsted acid and applied to the Br?nsted acid-catalyzed Mukaiyama aldol and Michael reactions with silyl enol ethers. The resulting Mukaiyama aldol products of aldehydes

Organotin perfluorooctanesulfonates as air-stable Lewis acid catalysts: Synthesis, characterization, and catalysis

The reactions of 1,3-dichloro-1,1,3,3-tetrabutyldistannoxane and di-alkyltin dihalides with silver perfluoro-octanesulfonate provided the corresponding sulfonates as hydrates. The number of water molecules (n) of hydration was dependent on the conditions. The distannoxane derivative was identified as n from 0.5 to 6, while in the hydrated mononuclear species and DMSO complexes n varied widely from 4 to 13. 119Sn NMR spectroscopy and conductivity measurements indicated the ionic dissociation of these compounds in solution. These compounds exhibited unusually high solubility in polar organic solvents. The ionic dissociation together with facile hydration probably causes the unusual solubility. The Lewis acidity of these compounds was found to be high among organotin derivatives on the basis of ESR spectra of Superoxide/ metal-ion complexes. In contrast to well-known organotin Inflates, these compounds suffered no hydrolysis upon storage in open air. The high catalytic activity of the distannoxane 1 was exemplified for various carboncarbon bond-forming reactions, such as Mukaiyama-aldol as well as -Michael reactions and allylation of aldehydes.

Magnesium Chloride-Promoted Michael Addition of Dimethylsilyl Enolates to α-Enones

In the presence of MgCl2, dimethylsilyl (DMS) enolates 1 smoothly reacted with α-enones in DMF to form 1,5-diketones 3 in moderate to high yields. The Michael addition proceeded with moderate to high anti-diastereoselectivity.

Michael addition of stannyl ketone enolate to α,β-unsaturated esters catalyzed by tetrabutylammonium bromide and an ab initio theoretical study of the reaction course

Michael addition of stannyl ketone enolates to α,β-unsaturated esters was accomplished in the presence of a catalytic amount of tetrabutylammonium bromide (Bu4NBr). Other typical systems using lithium enolate or silyl enolate with catalysts (TiCl4 or Bu4NF) failed to give the desired products. The bromide anion from Bu4NBr coordinates to the tin center in enolate to accelerate the conjugate addition where a five-coordinated tin species was generated. The coordination of the bromide anion significantly raises the HOMO level of tin enolate and enhances its nucleophilicity. The conjugate addition provides the intermediate Michael adduct, which has an ester enolate moiety, and the adduct immediately transforms to α-stannyl γ-ketoester by keto - enol tautomerization. This step contributes to the stabilization of the product system and leads to a thermodynamically favorable reaction course. An ab initio calculation reveals that the activation energy in the reaction using the bromide anion is lower than that of the reaction without using it. The transition state in either reaction course has a linear structure, not a cyclic one. This system can be applied to a variety of tin enolates and α,β-unsaturated carbonyls involving enoates, enones, and unsaturated amides.

Aluminum bis(trifluoromethylsulfonyl)amides: New highly efficient and remarkably versatile catalysts for C-C bond formation reactions

Superacid-derived aluminum catalysts R2AlNTf2 (2-5 mol%) are highly efficient and versatile and are suitable promoters for the allylation and pentadienylation of aldehydes, aldol reactions, aldol cross-coupling of ketones, and Michae

Indium-trichloride catalyzed Michael reaction of silyl enol ethers with α,β-unsaturated carbonyl compounds under neat condition

In the presence of a catalytic amount of indium (III) trichloride (InCl3) (20 mol%), ketene silyl enol ethers react quickly with α, β- unsaturated ketones and esters to afford the corresponding Michael adducts in moderate to good yields. Indium(III) trichloride can be recovered and reused without decrease in yields.