4463-26-7

Upstream product

• 4342-61-4 1,2-dichlorotetramethylsilane 
• 1711-06-4 3-Methylbenzoyl chloride 
• 99-04-7 m-Toluic acid 
• 591-17-3 meta-bromotoluene 
• 59417-06-0 1,4-dimethyl-2,3-dioxopiperazine 
• 79-37-8 oxalyl dichloride 
• 28987-79-3 m-tolylmagnesium bromide 
• 1218-85-5 3,3'-dimethylbenzoin 
• 2765-16-4 bis(3-methylphenyl)acetylene 
• 61560-94-9 3-methylphenyloxoacetic acid 
• 64196-54-9 3,3'-Dimethyldesoxybenzoin 
• 585-74-0 3-Methylacetophenone 
• 24133-60-6 3,3'-Dimethyl-α,α'-dihydroxybibenzyl 
• 625-95-6 3-Iodotoluene 

Downstream Products

• 4393-23-1 3,3'-dimethyl-benzilic acid 
• 25379-20-8 2-phenylindolizine 
• 83260-58-6 2,3-Di-m-tolyl-quinolizinylium; bromide 
• 24133-60-6 (S,R)-1,2-di-m-tolylethane-1,2-diol 
• 87383-53-7 2,3-Bis<3-(brommethyl)phenyl>chinoxalin 
• 122344-93-8 5,5-bis(3-methylphenyl)hydantoin 
• 1318238-32-2 ethyl 2,2-di(m-tolyl)acetate 
• 1298054-21-3 C₂₈H₂₀N₂O 
• 87383-52-6 2,3-Bis(3-methylphenyl)chinoxalin 

Relevant academic research and scientific papers

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

Photo-induced oxidative cleavage of C-C double bonds of olefins in water

The carbonyl compounds, synthesized by the oxidative cleavage of their corresponding olefins, are of great significance in organic synthesis, especially aryl ketones. We have developed a gentle and effective protocol, using acid red 94 as the organic metal-free photocatalyst, O2 as the oxidant, and water as the solvent. Under visible light irradiation, aryl ketone derivatives were obtained in moderate to excellent yields, showing good economic and environmental advantages.

Isostructurality of quinoxaline crystal phases: The interplay of weak hydrogen bonds and halogen bonding

Tailoring the physical properties of molecular crystals though the construction of solid solutions requires the existence of isostructural crystals. Simple substitutions of a given molecular framework can give a range of different crystal structures. A se

Conversion of alkynes into 1,2-diketones using HFIP as sacrificial hydrogen donor and DMSO as dihydroxylating agent

A metal-free and hypervalent iodine free conversion of internal alkynes into 1,2-diketo compounds has been described. The efficacy of the present protocol rely on the use of HFIP (1,1,1,3,3,3-Hexafluoro-2-propanol) as reducing agent of alkynes and DMSO as dihydroxylating agent of olefins to acquire the desired chemical transformations. The obtained 1,2-diketones were further transformed into useful derivatives.

Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).

Silver-Catalyzed Decarboxylative Couplings of Acids and Anhydrides: An Entry to 1,2-Diketones and Aryl-Substituted Ethanes

Silver-catalyzed oxidative decarboxylative couplings of carboxylic acids and anhydrides to produce 1,2-diketones and substituted ethanes were developed. This reaction allows the generation of acyl or alkyl radicals by decarboxylation of the corresponding α-keto acids, alkyl acids and anhydrides, which are sequentially coupled to efficiently construct a new C?C bond. This reaction represents a carboxylic acid decarboxylative alternative that employs a radical termination strategy. (Figure presented.).

Reaction control in heterogeneous catalysis using montmorillonite: Switching between acid-catalysed and red-ox processes

The use of montmorillonite, modified with a super-acid (CF3SO3H), in the presence of hydroquinone as a radical scavenger and under a nitrogen atmosphere, induced the formation of tetrasubstituted furans as the major product from benzoins. In the absence of a radical scavenger, the only products obtained were 1,2-diketones.

Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds

A highly enantioselective hydrosilylation of 1,2-dicarbonyl compounds was successfully realized for the first time utilizing the combination of tricyclohexylphosphine and chiral alkenylborane derived in situ from diyne as a frustrated Lewis pair catalyst. A variety of optically active α-hydroxy ketones and esters were obtained in 52-98% yields with 86-99% ee's.

Highly efficient asymmetric hydrogenation of cyano-substituted acrylate esters for synthesis of chiral γ-lactams and amino acids

A highly efficient and enantioselective synthesis of γ-lactams and γ-amino acids by Rh-catalyzed asymmetric hydrogenation has been developed. Using the Rh-(S,S)-f-spiroPhos complex, under mild conditions a wide range of 3-cyano acrylate esters including both E and Z-isomers and β-cyano-α-aryl-α,β-unsaturated ketones were first hydrogenated with excellent enantioselectivities (up to 98% ee) and high turnover numbers (TON up to 10 000).

Copper-catalyzed direct synthesis of diaryl 1,2-diketones from Aryl iodides and propiolic acids

Benzil derivatives such as diaryl 1,2-diketones are synthesized via the direct decarboxylative coupling reaction of aryl propiolic acids and their oxidation. The optimized conditions are that the reaction of aryl propiolic acids and aryl iodides is conducted at 140°C for 6 h in the presence of 10 mol % CuI/Cu(OTf)2 and Cs2CO3, after which HI (aq) is added and further reacted. The method shows good functional group tolerance toward ester, aldehyde, cyano, and nitro groups. In addition, symmetrical diaryl 1,2-diketones are obtained from aryl iodides and propiolic acid in the presence of palladium and copper catalysts.