34082-43-4

Upstream product

• 74552-54-8 2-Hydroxy-2-(2-methoxyphenyl)-1-phenylethanone 
• 100-52-7 benzaldehyde 
• 135-02-4 ortho-anisaldehyde 
• 6969-02-4 [3-(4-methoxyphenyl)oxiran-2-yl]phenylmethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 529-28-2 4-iodoanisol 
• 637-44-5 phenylpropyolic acid 
• 536-74-3 phenylacetylene 
• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 27356-33-8 2-(2-methoxyphenyl)-1-phenylethan-1-one 
• 100-66-3 methoxybenzene 
• 103-80-0 phenylacetyl chloride 
• 33470-10-9 1-(2-methoxyphenyl)-2-phenylethanone 
• 591-50-4 iodobenzene 

Downstream Products

• 34589-99-6 2-hydroxybenzil 
• 108475-94-1 2-methoxy-benzilic acid 
• 135147-78-3 1-(2-methoxyphenyl)-2-phenylethanedione dioxime 
• 27356-33-8 2-(2-methoxyphenyl)-1-phenylethan-1-one 
• 74552-54-8 2-Hydroxy-2-(2-methoxyphenyl)-1-phenylethanone 
• 55913-05-8 2-hydroxy-1-(2-methoxyphenyl)-2-phenylethan-1-one 
• 1374852-03-5 (S)-2-hydroxy-1-(2-methoxyphenyl)-2-phenylethanone 
• 135147-79-4 erythro-1-(2-methoxyphenyl)-2-phenyl-1,2-ethanediamine dihydrochloride 
• 113180-52-2 2-[2-(2-Oxo-2-phenyl-acetyl)-phenoxy]-propionic acid 

Relevant academic research and scientific papers

Electrochemical oxidation-induced benzyl C–H carbonylation for the synthesis of aromatic α-diketones

Electrochemical oxidation-induced direct carbonylation of benzyl C–H bond for the synthesis of aromatic α-diketones is described. In this process, tetrabutylammonium iodide (nBu4NI) not only acts as an electrolyte, but its iodine anion is oxidized to an iodine radical at the anode, acting as a hydrogen atom transfer agent. The iodine radical extracts the benzyl hydrogen atom and causes the carbonylation of the benzyl position, where O2 in the air is used as an oxygen source.

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.

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles

Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph3PAuNТf2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.

Ring Closing Metathesis Approach for the Synthesis of o-Terphenyl Derivatives

A linear synthesis of o-terphenyl derivatives has been delineated using ring closing metathesis (RCM) as the key step. In this approach, benzil derivatives upon allyl Grignard addition provides diphenyl-1,2-diallyl dihydroxy derivatives which undergo ring closing metathesis to afford tetrahydro terphenyl derivatives. Aromatization-driven dehydration then leads to a diverse set of electron rich and electron deficient o-terphenyls. Furthermore, oxidative coupling of electron rich o-terphenyls provides the corresponding triphenylene derivatives.

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.

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.

Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy

A gold-catalyzed intermolecular alkyne oxidation for the preparation of 3-coumaranones has been developed. Using 8-isopropylquinoline N-oxides as oxidants, the reactions of o-ethynylanisoles afford versatile 3-coumaranones in moderate to good isolated yields. The synthetic utility of this chemistry is also indicated by the synthesis of the natural product sulfuretin.

Practical approach for preparation of unsymmetric benzils from β-ketoaldehydes

An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones from β-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite.