59790-53-3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 577-16-2 2-Methylacetophenone 
• 529-20-4 2-methylphenyl aldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 1234571-83-5 3-hydroxy-1-(2-methylphenyl)-3-phenylpropan-1-one 
• 1228555-44-9 (R)-3-hydroxy-1-(2-methylphenyl)-3-phenylpropan-1-one 
• 1616350-41-4 2-(1-benzoyl-5-methyl-2-phenyl-1H-indol-4-yl)-1-(o-tolyl)ethanone 
• 42070-90-6 (R)-1-(2-methylphenyl)ethanol 
• 35276-81-4 3-oxo-3-(o-tolyl)propanenitrile 
• 7287-82-3 1-O-tolyl-ethanol 
• 145070-48-0 α-hydroxy-2'-methylacetophenone 
• 1010691-60-7 (R)-methyl 2-hydroxy-2-methyl-4-oxo-4-(2-methylphenyl)butanoate 
• 96746-06-4 trans-2-(2-methylbenzoyl)-3,6-dihydro-4,5-dimethyl-2H-thiapyran 1-oxide 
• 96746-05-3 cis-2-(2-methylbenzoyl)-3,6-dihydro-4,5-dimethyl-2H-thiapyran 1-oxide 

Relevant academic research and scientific papers

β-Diazocarbonyl Compounds: Synthesis and their Rh(II)-Catalyzed 1,3 C?H Insertions

Herein, we describe the first electrophilic diazomethylation of ketone silyl enol ethers with diazomethyl-substituted hypervalent iodine reagents that gives access to unusual β-diazocarbonyl compounds. The potential of this unexplored class of diazo compounds for the development of new reactions was demonstrated by the discovery of a rare Rh-catalyzed intramolecular 1,3 C?H carbene insertion that led to complex cyclopropanes with excellent stereocontrol.

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.

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.).

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.

Visible light-induced palladium-catalyzed ring opening β-H elimination and addition of cyclobutanone oxime esters

A palladium catalyst under visible light irradiation activates cyclobutanone oxime ester through single electron transfer to induce radical ring opening to generate hybrid cyanoalkyl Pd(i) radical species. Hybrid cyanoalkyl Pd(i) radical species can undergo either β-H elimination to deliver (E)-4-arylbut-3-enenitrile or undergo radical addition with silyl enol ether and enamide to generate δ-cyano ketones. A dual ligand system composed of two phosphine ligands is essential for the high reactivity.

FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers

Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6-tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ-terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).

Photoredox-Catalyzed Decarboxylative Alkylation of Silyl Enol Ethers to Synthesize Functionalized Aryl Alkyl Ketones

Photoredox-catalyzed decarboxylative alkylation of silyl enol ethers has been developed. Diverse functionalized aryl alkyl ketones were afforded in modest to good yields using N-(acyloxy)phthalimide as an easy access alkyl radical source under mild and operationally simple conditions. The excellent performance of drug molecules such as fenbufen and indomethacin and naturally occurring carboxylic acids such as stearic acid and dehydrocholic acid further demonstrated the practicability of the reaction.

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones

The FeIII- or AgI-catalyzed oxidative fluorination of cyclopropanols via radical rearrangement is disclosed. This process features a straightforward and highly effective protocol for the site-specific synthesis of β-fluoroketones and represents an expedient method for the synthesis of γ-, δ- and ε-fluoroketones. Notably, this reaction proceeds at room temperature and tolerates a diverse array of cyclopropanols.