3834-64-8

Upstream product

• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 100-52-7 benzaldehyde 
• 64345-69-3 2-fluorostilbene 
• 258499-09-1 1-(2'-fluorophenyl)-3-phenylpropane-1,3-dione 
• 3826-47-9 2-(2-fluorophenyl)-1-phenylethan-1-one 
• 326-62-5 2-fluorophenyl acetonitrile 
• 348-52-7 1-Fluoro-2-iodobenzene 
• 536-74-3 phenylacetylene 
• 29778-27-6 (2-(2-fluorophenyl)ethynyl)benzene 
• 702701-86-8 1-(2-fluorophenyl)-2-oxo-2-phenylethyl benzoate 
• 702701-95-9 2-(2-fluorophenyl)-2-hydroxy-1-phenylethan-1-one 
• 144461-81-4 2-(α-hydroxy-2-fluorobenzyl)-2-phenyl-1,3-dithiane 

Downstream Products

• 70028-82-9 5-(2-fluorophenyl)-5-phenylhydantoin 
• 1580052-27-2 C₁₄H₁₃FO₂ 

Relevant academic research and scientific papers

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.

Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds

Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Br?nsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.

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.

Selectfluor-Mediated Simultaneous Cleavage of C-O and C-C Bonds in α,β-Epoxy Ketones under Transition-Metal-Free Conditions: A Route to 1,2-Diketones

Selectfluor-mediated simultaneous cleavage of C-O and C-C bonds in α,β-epoxy ketones has been successfully achieved under transition-metal-free conditions. The reaction gives 1,2-diketone compounds in moderate to good yields involving a ring-opening/benzoyl rearrangement/C-C bond cleavage sequence under oxidative conditions.

Asymmetric transfer hydrogenation of unsymmetrical benzils

In this paper, the asymmetric transfer hydrogenation of unsymmetrical benzils with m, p-substituents was conducted with a substrate/catalyst molar ratio of 100 at 40°C for 24 h to produce (S,S)-hydrobenzoins in good yields (76.2% to 97.1%) with high diastereomeric (syn/anti = 10.8 to 29.7/1) and enantiomeric purities (86.1%ee syn to 98.9%ee syn). Unfortunately, the unsymmetrical benzils with the o-substituents such as electron-donating (R = CH3, OCH3) and electron-withdrawing groups (R = F, Cl, CF3) resulted in poor yields (0% to 31.2%), even at 40°C for 72 h. These products had inefficient diastereoselectivities (syn/anti = 1.5 to 5.0/1) caused by steric effects. Furthermore, the results of a dynamic-kinetic study were used to propose a plausible reaction pathway of unsymmetrical benzil using 3-methoxy-1,2-diphenyl ethanedione as an example.

Gold-catalyzed synthesis of benzil derivatives and α-keto imides via oxidation of alkynes

An efficient process based on the gold-catalyzed redox reaction has been developed to oxidize 1,2-diarylacetylene or ynamide to 1,2-diaryldiketone or α-keto imide respectively. This process can tolerate a variety of functional groups and affords 1,2-dicarbonyl compounds in excellent yields under mild reaction conditions.

Ruthenium-catalyzed oxidation of alkenes at room temperature: A practical and concise approach to α-diketones

Chemical equations presented. The catalytic oxidation of alkenes to α-diketones is unprecedented. A new oxidation of alkenes, catalyzed by a ruthenium complex, which allows an efficient route to α-diketones using TBHP as an oxidant is described. This methodology is highly functional group tolerant, is practically convenient, requires no additional ligand, and operates under mild conditions with short reaction times. Based upon experimental observations, a plausible mechanism is proposed.

Mild oxidation of diarylacetylenes to 1,2-diketones using oxone in trifluoroacetic acid

A variety of 1,2-diaryldiketones were synthesized in 15-90% yields by treatment of diarylacetylenes with Oxone as the oxidant in trifluoroacetic acid. Oxidation of 1-nitro-2-(phenylethynyl) benzene and 2,4￠-(ethyne-1,2-diyl) bis(nitrobenzene) furnished 1-benzoylbenzo[c]isoxazol-3(1H)-one and benzo[c]isoxazol-3-yl(4-nitrophenyl)methanone as the major products, respectively. Georg Thieme Verlag Stuttgart.

A convenient and selective synthesis of unsymmetrical benzoins via the cyanide ion catalyzed cleavage of benzils

The cyanide ion-catalyzed cleavage of benzils is used for the generation of various 'masked' acyl intermediates. The reaction of these intermediates with various aldehydes furnishes the corresponding esters of unsymmetrical benzoins in very good yields. A variety of unsymmetrical benzoin derivatives are synthesized in this way, including ferrocene derivatives. The hydrolysis of benzoin esters and their subsequent oxidation affords the corresponding unsymmetrical benzoins and benzils in high yield.

A convenient preparation of symmetrical and unsymmetrical 1,2-diketones: Application to fluorinated phenytoin synthesis

1,2-Diketones are efficiently produced in two steps by reaction of aldehydes with anions derived from 2-substituted dithianes followed by treatment of the resulting alcoholis with NBS in aqueous acetone; phenytoin derivatives were prepared from these diketones by a standard method involving treatment with urea and potassium hydroxide under reflux.