40103-79-5

Upstream product

• 14635-91-7 1-methyl-3-(2-phenylethynyl)benzene 
• 93-98-1 N-phenyl benzoyl amide 
• 620-23-5 m-tolyl aldehyde 
• 585-74-0 3-Methylacetophenone 
• 14064-48-3 (E)-3-methylstilbene 
• 591-50-4 iodobenzene 
• 3029-79-6 3-methylcinnamic acid 
• 591-17-3 meta-bromotoluene 
• 98-86-2 acetophenone 
• 95606-81-8 2-phenyl-1-(m-tolyl)ethan-1-one 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 34403-03-7 1-phenyl-2-(meta-tolyl)ethanone 
• 2947-60-6 3-methylbenzyl cyanide 
• 108-86-1 bromobenzene 

Downstream Products

• 1372805-92-9 C₁₇H₁₇N₃O 

Relevant academic research and scientific papers

Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils

The conversion of 1,3-diaryl-2-diazo-1,3-diketones to 1,2-daryl-1,2-diketones (benzils) is reported based on a rhodium(II)-catalyzed aerobic decomposition process. The reaction occurs at ambient temperatures and can be catalyzed by a few dirhodium carboxylates (5 mol %) under a balloon pressure of oxygen. Moreover, an oxygen atom from the O2 reagent is shown to be incorporated into the product, and this is accompanied by the extrusion of a carbonyl unit from the starting materials. Mechanistically, it is proposed that the decomposition may proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone were synthesized from the corresponding diazo substrates in varying yields. On the other hand, the method did not allow the generation of benzocyclobutene-1,2-dione from 2-diazo-1,3-indandione because of the difficulty of inducing the initial rearrangement.

Aerobic oxygenation of α-methylene ketones under visible-light catalysed by a CeNi3complex with a macrocyclic tris(salen)-ligand

A hetero-tetranuclear CeNi3 complex with a macrocyclic ligand catalysed the aerobic oxygenation of a methylene group adjacent to a carbonyl group under visible-light radiation to produce the corresponding α-diketones. The visible-light induced homolysis of the Ce-O bond of a bis(enolate) intermediate is proposed prior to aerobic oxygenation.

Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones

A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

Synthesis of 1,2-diketones by mercury-catalyzed alkyne oxidation

The first mercury-catalyzed synthesis of 1,2-diketones by alkyne oxidation has been developed. This inexpensive method extends the potential of mercury catalysis and allows the rapid construction of various 1,2-diketones and α-carbonyl amides in good yields with high functional group tolerance.

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.

Synthesis of unsymmetrical benzilsviapalladium-catalysed a-arylation-oxidation of 2-hydroxyacetophenones with aryl bromides

A diverse set of unsymmetrically substituted benzils were facilely synthesised by a cross-coupling reaction between 2-hydroxyacetophenones and aryl bromides in the presence of a palladium catalyst. Experimental studies suggested a reaction mechanism involving a one-pot tandem palladium-catalysed a-arylation and oxidation, where aryl bromides play a dual role as mild oxidants as well as arylating agents.

Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles

An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.

Preparing method of photocatalytic alpha-diketone compound

The invention belongs to the technical field of medical and chemical intermediates and related chemicals, and provides a preparing method of photocatalytic alpha-diketone compound. Phenylacetylene and the derivative thereof are used as raw materials, and under the lighting condition, under the combined action of a semiconductor photocatalyst and an additive, alpha-diketone compound is generated through air oxygen in organic solvent. The preparing method has the advantages of being easy to operate, mild in condition and environmentally friendly, has probability of industrialization and obtains the alpha-diketone compound at the high yield, and the catalyst is recyclable. The alpha-diketone compound synthesized through the method can be further functionalized to obtain various compounds applied to development and research of natural products, function materials and fine chemicals.

A method for synthesizing derivatives benzil

The invention discloses a method for synthesizing a benzil derivative. The method comprises the following steps: adding epoxy chalcone compound shown in the formula I, a Selectfluor oxidizing agent and inorganic base into a mixed solvent of acetonitrile and water, stirring for reaction for 4-8 h at 60-100 DEG C, and treating a reaction liquid obtained after the reaction is finished to prepare the benzil derivative shown in the formula II. The synthesis method has the advantages that the raw materials are cheap and easy to obtain, transition metal catalysis is not needed, the oxygen source is easy to obtain and environment-friendly, the reaction condition is mild, the target substrate can be synthesized efficiently, the universality of the functional group is good, and the operation is simple and convenient.

1,2-diaryl ethylenediamine compound preparation method

The invention discloses a 1,2-diaryl ethylenediamine compound preparation method, which comprises: (1) under the catalysis of B(C6F5)3, by adopting H2 as a reduction agent, carrying out a reduction reaction on a compound represented by a formula II to obtain a compound (1,2-diaryl ethylenediamine compound) represented by a formula I, wherein Ar1 and Ar2 in the formulas I and II are phenyl or substituted phenyl, the substituting position of the substituting group is any one or any two selected from ortho, meta and para in the substituted phenyl, and the substituting group is methyl, methoxy, fluorine atom or bromine atom. According to the present invention, B(C6F5)3 is adopted as the catalyst and the 1,2-diaryldiimine is adopted as the substrate to synthesize the 1,2-diaryl ethylenediamine compound in the high-yield and high-diastereoselectivity (dr is more than 99:1) manner; and the method has characteristics of easily available raw materials, mild reaction conditions, high reaction activity, wide substrate application range, and great industrial potential.