3834-65-9

Upstream product

• 119072-55-8 tert-butylisonitrile 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 841-76-9 triphenylaluminium 
• 29778-28-7 1-fluoro-3-(2-phenylethynyl)benzene 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 17763-67-6 Phenyl triflate 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 591-50-4 iodobenzene 
• 347-90-0 2-(3-fluorophenyl)-1-phenylethan-1-one 
• 501-00-8 3-fluorophenylacetonitrile 
• 455-36-7 1-(3-fluorophenyl)ethanone 
• 93-98-1 N-phenyl benzoyl amide 
• 456-48-4 3-Fluorobenzaldehyde 
• 100-52-7 benzaldehyde 

Downstream Products

• 1372805-91-8 C₁₆H₁₄FN₃O 
• 70028-84-1 5-(3-fluorophenyl)-5-phenylhydantoin 

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.

Palladium-Catalyzed Synthesis of 1,2-Diketones from Aryl Halides and Organoaluminum Reagents Using tert-Butyl Isocyanide as the CO Source

In this work, an interesting and practical procedure for the synthesis of 1,2-diketones from aryl halides and organoaluminum reagents has been developed. Employing tert-butyl isocyanide as the CO source and palladium as the catalyst, the desired 1,2-diketones were isolated in good to excellent yields with good functional group tolerance. Concerning the reaction partners, besides aryl halides, both alkyl- A nd arylaluminum reagents were all suitable substrates here.

Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines

We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.

Method for synthesizing benzil derivatives

The invention discloses a method for synthesizing benzil derivatives. The method comprises the steps that a diphenyl acetylene compound, halogenated ammonium salt or iodine chloride and a sulfur source serve as reactants, the reactants react in a solvent for a period of time, purification is conducted, and then the benzil derivatives are obtained. According to the method, a metal catalyst and toxic iodine are not used, the applied reactants are low in price, poisonless and tasteless, the operation method is simple, the yield is high, aftertreatment is easy, and the method is suitable for industrial production.

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.

Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions

We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.

NH4I/EtOCS2K promoted synthesis of substituted benzils from diphenylacetylene derivatives

A facile protocol is described for the synthesis of benzil derivatives from readily accessible diarylacetylene derivatives using the NH4I/EtOCS2K system. This novel protocol results in excellent chemoselectivity and provided good to excellent yields. A control experiment indicated that the reaction proceeds via NH4I promoted EtOCS2K dimerization to give the corresponding dixanthogen and subsequent dixanthogen assisted oxidation.

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.

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.

Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts

Both alkylarylalkynes and diarylalkynes 1 are converted into the α-diketones 2 in good yield by the use of mercuric salts, e.g., mercuric nitrate hydrate or mercuric triflate, in the presence of water. Other mercuric salts, e.g., sulfate, chloride, acetate, or trifluoroacetate, do not provide the diketone product. A possible mechanism is proposed.