97405-27-1

Upstream product

• 99-04-7 m-Toluic acid 
• 618-47-3 m-toluamide 
• 624-31-7 4-tolyl iodide 
• 443638-87-7 N-(3-methylbenzoyl)-8-aminoquinoline 
• 99-99-0 1-methyl-4-nitrobenzene 
• 17933-03-8 m-tolylboronic acid 
• 13939-06-5 molybdenum hexacarbonyl 
• 201230-82-2 carbon monoxide 
• 106-49-0 p-toluidine 
• 539-44-6 N-4-methylphenylhydrazine 
• 61560-94-9 3-methylphenyloxoacetic acid 
• 585-74-0 3-Methylacetophenone 
• 25109-04-0 1-(p-tolyl)-1,2,3,4-tetrazole 
• 620-23-5 m-tolyl aldehyde 

Relevant academic research and scientific papers

Switching from biaryl formation to amidation with convoluted polymeric nickel catalysis

A stable, reusable, and insoluble poly(4-vinyl-pyridine) nickel catalyst (P4VP-NiCl2) was prepared through the molecular convolution of poly(4-vinylpyridine) (P4VP) and nickel chloride. We proposed a coordination structure of the Ni center in the precatalyst based on elemental analysis and Ni K-edge XANES, and we confirmed that it is consistent with Ni K-edge EXAFS. The Suzuki?Miyaura-type coupling of aryl halides and arylboronic esters proceeded using P4VP-NiCl2 (0.1 mol % Ni) to give the corresponding biaryl compounds in up to 94% yield. Surprisingly, when the same reaction of aryl halides and arylboronic acid/ester was carried out in the presence of amides, the amidation proceeded predominantly to give the corresponding arylamides in up to 99% yield. In contrast, the reaction of aryl halides and amides in the absence of arylboronic acid/ester did not proceed. P4VP-NiCl2 successfully catalyzed the lactamization for preparing phenanthridinone. P4VP-NiCl2 was reused five times without significant loss of catalytic activity. Pharmaceuticals, natural products, and biologically active compounds were synthesized efficiently using P4VPNiCl2 catalysis. Nickel contamination in the prepared pharmaceutical compounds was not detected by ICP-MS analysis. The reaction was scaled to multigrams without any loss of chemical yield. Mechanistic studies for both Suzuki?Miyaura and amidation were performed.

Palladium-Catalyzed Amide Synthesis via Aminocarbonylation of Arylboronic Acids with Nitroarenes

A palladium-catalyzed aminocarbonylation of aryl boronic acids with nitroarenes for the synthesis of amides has been developed. A wide range of substrates were well-tolerated and gave the corresponding amides in moderate to good yields. No external oxidant or reductant was needed in this procedure. This procedure provides a redox-economical process for the synthesis of amides.

An efficient, one-pot transamidation of 8-aminoquinoline amides activated by tertiary-butyloxycarbonyl

The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C(acyl)–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.

Synthesis of Secondary Amides through the Palladium(II)-Catalyzed Aminocarbonylation of Arylboronic Acids with Amines or Hydrazines and Carbon Dioxide

A new Pd-catalyzed aminocarbonylation of arylboronic acids with amines or phenylhydrazines has been developed. Various secondary amides were produced from readily available substrates and cheap common metal catalysts in a CO atmosphere (balloon). Remarkably, we presents the first example of aminocarbonylations between arylboronic acids and phenylhydrazines.

Method for synthesizing N-aryl aromatic amide by adopting aromatic hydrazine

The invention discloses a method for synthesizing N-aryl aromatic amide by adopting aromatic hydrazine. The method includes that arylboronic acid, the aromatic hydrazine, a primary catalyst and an auxiliary catalyst are added in a solvent, the N-aryl aromatic amide as is indicated in the formula III is obtained by performing separation and purification after heating reflux reaction, and CO is fedto a reaction to enable pressure of the reaction system to be 0.1-5MPa during reaction. The method is concise and efficient, phenylhydrazine is substituted, organic boronic acid and CO which are stable in air and easy to obtain are taken as raw materials, metal palladium is taken as the primary catalyst, copper or iron is taken as the auxiliary catalyst, and the N-aryl aromatic amide is synthesized efficiently under mild reaction conditions.

Silver-promoted decarboxylative amidation of α-keto acids with amines

A general and effective method for the synthesis of amides through decarboxylative amidation of α-keto acids with amines has been developed. The reaction proceeded smoothly to afford the corresponding amide products in good yield under air and shows excellent functional group tolerance. In addition, the protocol can be further applied in the synthesis of heterocyclic compounds like benzimidazoles.

Synthesis of amides through an oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions

A simple, inexpensive and efficient one-pot synthesis of amides was achieved in good yields via the direct oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions.

Identification of a potent and noncytotoxic inhibitor of melanin production

On the basis of a hit from random screening, biaryl amide derivatives were prepared in a combinatorial manner via parallel solution-phase synthesis, and their effects on melanocytes were investigated to discover new effective skin depigmenting agents. Amo

Iron-catalyzed N-arylations of amides

A method was proposed for iron-catalyzed N-arylation of primary amides and its applicability to the synthesis of N-heterocycles by intramolecular ring closures. The method used a catalyst system of 10 mol % of FeCl3 and 20 mol % of N,N'-dimethylethylenediamine (DMEDA). The study found that secondary amides of N-methylbenzamide and N-benzylbenzamide produce N-arylated products in trace amounts. The method developed an iron-based catalyst system for efficient N-arylations of primary amides with aryl iodides. The study used a sealable tube equipped with a magnetic stir bar charged with amide, or K 3PO4, or K2CO3, or FeCl3. The study used NMR spectroscopic analysis to determine the identity and purity of the products. The method observed that different substituted aryl iodides made a positive impact on the reaction.

Nickel-catalyzed coupling of isocyanates with 1,3-iodoesters and halobenzenes: A novel method for the synthesis of imide and amide derivatives

Substituted imide and amide derivatives were conveniently prepared from the reaction of isocyanates with o-iodobenzoates and haloarenes catalyzed by the NiBr2(dppe)/dppe/Zn system in moderate to good yields with excellent tolerance of functional groups. The Royal Society of Chemistry 2005.