16738-12-8

Upstream product

• 879-18-5 naphthalene-1-carbonic acid chloride 
• 18166-02-4 N-trimethylsilylmethylamine 
• 124-38-9 carbon dioxide 
• 88313-80-8 naphthalen-1-yl(trimethylsilyl)methanone 
• 5781-53-3 monomethyl oxalyl chloride 
• 91-20-3 naphthalene 
• 67-56-1 methanol 
• 553-90-2 Dimethyl oxalate 
• 90-11-9 1-Bromonaphthalene 
• 941-98-0 1'-naphthacetophenone 
• 370561-84-5 methyl 2-diazo-2-(naphthalen-1-yl)acetate 
• 13158-05-9 (+/-)-Methyl α-methoxy-α-(1-naphthyl)acetate 
• 2876-78-0 methyl 1-naphthylacetate 
• 78772-53-9 methyl 2-hydroxy-2-(naphthalen-1-yl)acetate 

Downstream Products

• 86-87-3 naphth-1-yl acetic acid 

Relevant academic research and scientific papers

Visible-Light-Induced Catalyst-Free Carboxylation of Acylsilanes with Carbon Dioxide

Intermolecular carbon-carbon bond formation between acylsilanes and carbon dioxide (CO2) was achieved by photoirradiation under catalyst-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of the acylsilanes added to the C═O bond of CO2 to give α-ketocarboxylates, which underwent hydrolysis to afford α-ketocarboxylic derivatives in good yields. Control experiments suggest that the generated siloxycarbene is likely to be from the singlet state (S1) of the acylsilane and the addition to CO2 is not in a concerted manner.

Preparation method of alpha-ketoester compound

The invention discloses a preparation method of an alpha-ketone ester compound. The method specifically comprises the following operation steps: adding raw materials alpha-diazo ester and an organic photocatalyst into a reaction flask, then adding an organic solvent, and reacting for 2-12 hours in air at room temperature under the irradiation of a visible light lamp; after the reaction is monitored by thin-layer chromatography (TLC), stopping the reaction, and extracting a reaction solution by using ethyl acetate; concentrating the extracting solution under reduced pressure to obtain a crude product, and performing column chromatography separation on the crude product to obtain the alpha-diazonium ester compound. According to the preparation method, clean visible light is used as reaction energy, cheap organic dye is used as a photocatalyst, air is used as a green oxidizing agent and an oxygen source, and the preparation method has the advantages of simplicity and convenience in operation, no metal residue and mild reaction conditions.

Preparation method of alpha-naphthylacetic acid

The invention relates to the technical field of organic synthesis, and provides a preparation method of alpha-naphthylacetic acid. The invention aims to solve the problem that preparation of alpha-naphthylacetic acid is not economical and environmentally friendly in the prior art. The preparation method comprises the following steps: (1) dissolving naphthalene and Lewis acid in a solvent, carryingout heating, adding oxalyl chloride monoester, and carrying out a reaction to generate alpha-acetonaphthone acid ester; and (2) adding the alpha-acetonaphthone acid ester obtained in the step (1) andhydrazine hydrate into a high-boiling-point alcohol solvent, carrying out a heating reaction, adding a strong base, continuing the heating reaction, and adjusting a pH value to an acidic state afterthe reaction is finished so as to obtain alpha-naphthylacetic acid. According to the method, naphthalene and oxalyl chloride monoester which are cheap and easy to obtain are used as raw materials, alpha-acetonaphthone acid ester is prepared under the action of Lewis acid, and then a series of reactions are performed under the action of hydrazine hydrate to generate alpha-naphthylacetic acid, so the use of highly toxic cyanide is avoided, highly toxic or foul gas is not generated in the reaction process, only one product is produced, reaction conditions are mild, yield is high and cost is low.

Copper(I)-catalyzed aerobic oxidation of α-diazoesters

A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.

CuO-catalyzed oxidation of aryl acetates with aqueous tert-butyl hydroperoxide for the synthesis of α-ketoesters

A practical method to access α-ketoesters from readily available aryl acetates is developed. In this approach, aqueous tert-butyl hydroperoxide and CuO are employed. No additional solvents are required and it was found that the peroxide side products in the reaction can be decomposed by pyridine.

I 2 /TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C-C Bond Cleavage

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I 2 /TBHP promoted sequential iodination, C-C bond cleavage, C-O bond formation and oxidation pathway is involved in this reaction.

Copper-catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates: Synthesis of aryl/heteroaryl α-keto esters

A copper catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates is described for the first time. This transformation represents a new route to synthesize α-keto esters, which are important intermediates for pharmaceuticals and organic synthesis. The reaction proceeds via in situ generation of a thionium ion that undergoes hydrolysis to furnish α-keto esters in synthetically viable yields (up to 82%).

Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides

A highly enantioselective iridium-catalyzed hydrogenation of α-keto amides to form α-hydroxy amides has been achieved with excellent results (up to >99% conversion and up to >99% ee, TON up to 100?000). As an example, this protocol was applied to the synthesis of (S)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol, the enantiomer of norepinephrine, which is widely used as an injectable drug for the treatment of critically low blood pressure. Density functional theory (DFT) calculations were also carried out to reveal the reaction mechanism.

Direct asymmetric hydrogenation of α-keto acids by using the highly efficient chiral spiro iridium catalysts

A new efficient and highly enantioselective direct asymmetric hydrogenation of α-keto acids employing the Ir/SpiroPAP catalyst under mild reaction conditions has been developed. This method might be feasible for the preparation of a series of chiral α-hydroxy acids on a large scale.

One-pot efficient synthesis of aryl α-keto esters from aryl-ketones

A novel one-pot synthesis of aryl α-keto esters was developed through oxidation of aryl-ketones using selenium dioxide, esterification accompanied by ketalization, and hydrolysis. Both aromatics and heteroaromatics gave good yields by this one-pot method.