55991-66-7

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 99-90-1 para-bromoacetophenone 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 

Downstream Products

• 55991-70-3 5-(4-bromo-phenyl)-furan-2,3-dione 
• 124902-90-5 N-<3-(p-bromophenyl)-3-oxopropyl>-N-methyl-1-propanesulfonamide 
• 139535-66-3 N-methyl-N-<2,2-dimethyl-5-oxo-5-(4-bromophenyl)-3-pentenyl>methanesulfonamide 
• 139535-65-2 N-methyl-N-<2,2-dimethyl-3-methoxy-5-oxo-5-(4-bromophenyl)pentyl>methanesulfonamide 
• 99391-15-8 C₁₇H₂₀BrNO₂Si 
• 183435-01-0 1-(4-Bromo-phenyl)-3-ethoxy-5-phenylselanyl-pent-4-yn-1-one 
• 62558-63-8 p-Bromphenacyliden-anil 
• 87221-69-0 (4-Bromo-phenyl)-(4,5-dimethyl-1-phenyl-1,2,3,6-tetrahydro-pyridin-2-yl)-methanone 
• 99940-35-9 1-(4-bromophenyl)-2-(phenylamino)ethan-1-ol 

Relevant academic research and scientific papers

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides

The ring opening of cyclopropanols is rarely used in multicomponent reactions. Herein we report the three-component reaction of cyclopropanols with alkenes and tert-butyl hydroperoxide (TBHP) catalyzed by an iron catalyst. This protocol enables the incorporation of both the β-carbonyl fragment and a peroxy unit across the C=C double bond regioselectively, thus allowing an efficient, facile access to 5-oxo peroxides. Modification of the biologically active molecules and various downstream derivatizations of the peroxides are also demonstrated.

Lewis Acid-Catalyzed Carbofunctionalization of Uncommon C, N-Diacyliminium Ions: Controlling Regio- And Enantioselectivity

The tricyclic azepino[1,2-a]indole acetates 7, readily accessible by visible-light-driven catalytic photooxygenation of cyclohepta[b]indoles 1, are convenient precursors to novel and uncommon cyclic C,N-diacyliminium ions 3. We report here the first Lewis

Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation

Visible-light-induced deaminative alkylation of Katritzky salts with silyl enol ethers has been developed. The reaction can proceed efficiently through electron donor–acceptor complex formation, avoiding the use of precious metal complexes or synthetically elaborate organic dyes. A series of functionalized γ-ketoesters was successfully obtained with good functional group tolerance and compatibility under mild and straightforward conditions.

Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2: H -cyclohepta [b] furan-2-ones with silyl enol ethers

We developed a procedure for the direct synthesis of 2-arylazulenes, which were obtained in moderate to excellent yields, by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with aryl-substituted silyl enol ethers. The structures of some 2-arylazulenes were clarified by single-crystal X-ray analysis. The 2-phenylazulene derivatives obtained by this study showed noticeable fluorescence in acidic media.

Aryl Pyrazoles from Photocatalytic Cycloadditions of Arenediazonium

A photocatalytic synthesis of 1,5-diaryl pyrazoles from arenediazoniums and arylcyclopropanols is reported. The reaction proceeded under mild conditions (rt, 20 min) with catalytic [Ru(bpy)3]2+ under blue-light irradiation and exhibited compatibility with several functional groups (e.g., I, SF5, SO2NH2, N3, CN) and perfect levels of regiocontrol. Mechanistic studies (luminescence spectroscopy, CV, DFT, radical trapping, quantum yield determination) documented an initial oxidative quenching of the excited photocatalyst and the operation of a radical-chain mechanism.

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

Defluorinative Ring-Opening Indolylation of Siloxydifluorocyclopropanes: Controlled Synthesis of α-Fluoro-β-Indolyl-Propanones for Carbazole Construction

A catalytic defluorinative ring-opening indolylation of siloxydifluorocyclopropanes was reported. It was found that AgBF4-catalyzed reaction of siloxydifluorocyclopropanes with indoles could be controlled to deliver α-fluoro-β-indolyl-propanones within 1.5 hours at room temperature. Cyclization of these α-fluoroketone derivatives were then carried out in the presence of trifluoroacetic anhydride in toluene at room temperature. Carbazoles were formed efficiently via an intramolecularly nucleophilic addition of the in situ formed enamine intermediate to the keto carbonyl, followed by a sequential hydrolysis and eliminations of trifluoroacetic acid and hydrogen fluoride. (Figure presented.).

C?O coupling of Malonyl Peroxides with Enol Ethers via [5+2] Cycloaddition: Non-Rubottom Oxidation

Malonyl peroxides act both as oxidants and reagents for C?O coupling in reactions with methyl and silyl enol ethers. In the proposed conditions, the oxidative C?O coupling of malonyl peroxides with enol ethers selectively proceeds, bypassing the traditional Rubottom hydroxylation of enol ethers by peroxides. It was observed that the oxidative [5+2] cycloaddition of malonyl peroxides and enol ethers is the key stage of the discovered process. Oxidative C?O coupling of silyl enol ethers leads to the formation of α-acyloxyketones with a free carboxylic acid group. A specially developed preparative one-pot procedure transforms ketones via silyl enol ethers formation and the following coupling into α-acyloxyketones with yields 35–88%. The acid-catalyzed coupling with methyl enol ethers gives remarkable products while retaining the easily oxidizable enol fragment. Furthermore, these molecules contain a free carboxylic acid group, thus these nontrivial products contain two usually incompatible acid and enol ether groups. (Figure presented.).

Photoredox-Catalyzed Generation of Sulfamyl Radicals: Sulfonamidation of Enol Silyl Ether with Chlorosulfonamide

A novel and practical photoredox-catalyzed generation of sulfamyl radicals followed by radical sulfonamidation of enol silyl ether has been described. Diverse functionalized β-ketosulfonamides were prepared in modest to excellent yields under mild and economic reaction conditions through the present catalytic protocol. Furthermore, the methodology developed provides an efficient and convenient approach to the synthesis of the antiseizure drug Zonisamide.