65648-94-4

Upstream product

• 1762-15-8 1-(naphthalen-2-yl)-2-phenylethanone 
• 110-86-1 pyridine 
• 67-64-1 acetone 
• 120425-23-2 2-hydroxy-1-(naphthalen-2-yl)-2-phenylethan-1-one 
• 103-80-0 phenylacetyl chloride 
• 118736-10-0 2-hydroxy-2-(naphthalen-2-yl)-1-phenylethanone 
• 83015-77-4 2-(naphthalen-2-yl)-1-phenylethan-1-one 
• 57114-80-4 1-(naphthalen-2-yl)-3-phenyl-propan-1,3-dione 
• 93-08-3 methyl 2-naphthyl ketone 
• 71-43-2 benzene 
• 580-13-2 2-bromonaphthalene 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 63571-96-0 S-ethyl 2-oxo-2-phenylethanethioate 
• 7519-88-2 2,4,6-tris-(2-naphthyl)boroxine 

Downstream Products

• 120887-02-7 [2]naphthyl-phenyl-ethanedione-dihydrazone 
• 62956-75-6 1,2,4-Triphenyl-3-(2'-naphthyl)-cyclopentadienon 
• 65648-95-5 (2-naphthyl)phenylhydroxyacetic acid 
• 65648-87-5 1,2,4-Triphenyl-3-(2'-naphthyl)-benzol 

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.

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.

1,2-dicarbonyl compound and synthesis method thereof

The invention discloses a method for synthesizing a 1,2-dicarbonyl compound (1,2-dicarbonylamide or alpha-diketone compound), wherein 1,2-dicarbonyl thioester compounds used as 1,2-dicarbonyl reagentsreact with amine compounds or boric anhydride compounds under appropriate conditions to respectively synthesize a series of 1,2-dicarbonyl compounds. According to the present invention, the 1,2-dicarbonyl compound is obtained by using the stable 1,2-dicarbonyl thioester compound as the dicarbonylation reagent through one-step construction under mild conditions, such that the disadvantage that thetraditional method uses the unstable alpha-carbonyl acyl chloride to synthesize the 1,2-dicarbonyl compound is avoided.

B2pin2-mediated copper-catalyzed oxidation of alkynes into 1,2-diketones using molecular oxygen

An intriguing aerobic oxidation of alkynes through copper catalysis is described, in which bis(pinacolato)diboron (B2pin2) played a dominant intermediary role in the formation 1,2-diketones. This novel protocol, which can be performed at room temperature, is versatile for various substituted alkynes, including diarylalkynes and arylalkylalkynes. The mechanism of this reaction was preliminarily investigated by control experiments.

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.

Efficient synthetic route to bisaryl ketones via copper-catalyzed C-C triple bonds cleavage

An efficient copper-catalyzed aerobic synthesis of bisaryl ketones from 1,2-diarylalkynes via C-C triple bonds cleavage has been demonstrated. The aniline compounds were found to be crucial in our conditions and a plausible mechanism was put forward. This reaction constitutes a new transformation from 1,2-diarylalkynes into bisaryl ketones with a practical, neutral, and mild synthetic approach.

One-pot synthesis of unsymmetrical benzils by oxidative coupling using selenium dioxide and p-toluenesulfonic acid monohydrate

The oxidative coupling of the α-carbon atom of aromatic ketones with unactivated arenes in the presence of selenium dioxide and p-toluenesulfonic acid monohydrate is described. A number of unsymmetrical benzils have been prepared in good yields (38-75 % with high regioselectivity. The generality and functional tolerance of this new protocol is demonstrated. The mechanistic pathway for the oxidative coupling reaction is also described. The reaction displays superiority in terms of minimization of steps with the C-C bond formation promoted by SeO2 and pTsOH·H2O. This method is advantageous as the reactants used as the solvent can be recovered. Copyright

Iron-promoted C - C bond cleavage of 1,3-diketones: A route to 1,2-diketones under mild reaction conditions

A conceptual method for the preparation of 1,2-diketones is reported. The selective C - C bond cleavage of 1,3-diketones affords the 1,2-diketones in high yields under mild reaction conditions in air by the use of FeCl3 as the catalyst and tert-butyl nitrite (TBN) as the oxidant without the use of solvent. The possible reaction mechanism is discussed. This protocol provides an expeditious route to the useful 1,2-diketones.

An efficient palladium-catalyzed synthesis of benzils from aryl bromides: Vinylene carbonate as a synthetic equivalent of glyoxal

An expedient synthetic procedure of benzil derivatives from aryl bromides was developed using vinylene carbonate as a glyoxal equivalent in a palladium-catalyzed reaction. The reaction involved a sequential diarylation of vinylene carbonate to form 4,5-diaryl-1,3-dioxol-2-one, ring-opening to benzoin derivative, and an oxidation process.

DABCO-catalyzed oxidation of deoxybenzoins to benzils with air and one-pot synthesis of quinoxalines

Aerobic oxidation of deoxybenzoins could be efficiently catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) with air as the sole oxidant to give the corresponding benzils in excellent yields. The effects of reaction conditions, such as different bases, temperature, time and solvent, on the yield of the product were investigated. Moreover, the process has been successfully extended to a one-pot synthesis of quinoxalines from benzyl ketones and aromatic 1,2-diamines. Georg Thieme Verlag Stuttgart New York.