5083-03-4

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 371-40-4 4-fluoroaniline 
• 1765-93-1 4-fluoroboronic acid 
• 619-55-6 para-methylbenzamide 
• 201230-82-2 carbon monoxide 
• 5720-05-8 4-methylphenylboronic acid 
• 371-14-2 4-fluorophenylhydrazine 
• 99-94-5 p-Toluic acid 
• 5084-80-0 tri(4-tolyl)boroxine 
• 65141-04-0 phenyl N-(4-fluorophenyl)carbamate 
• 350-46-9 4-Fluoronitrobenzene 
• 35980-25-7 N-(4-fluorophenyl)-2,2,2-trifluoro-acetamide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 24075-34-1 4-fluorophenyl isocyanide 

Downstream Products

• 1239751-54-2 C₁₄H₇ClFNOS 
• 1370531-57-9 methyl (2S)-1-[4-(6-fluoro-1,3-benzothiazol-2-yl)benzoyl]tetrahydro-1H-2-pyrrolecarboxylate 
• 1239752-25-0 4-(6-fluoro-1,3-benzothiazol-2-yl)benzoic acid 
• 1239772-93-0 2-[4-(bromomethyl)phenyl]-6-fluoro-1,3-benzothiazole 
• 146274-09-1 N-(4-fluorophenyl)-4-methylbenzothioamide 

Relevant academic research and scientific papers

Direct amide synthesis: via Ni-mediated aminocarbonylation of arylboronic acids with CO and nitroarenes

Herein we describe an alternative and unconventional approach of an aminocarbonylation reaction to access aryl amides from readily available and low-cost arylboronic acids and nitroarenes. Nickel metal can serve as both reductant and catalyst in this direct aminocarbonylation. This protocol exhibits a good functional group compatibility and allows a variety of aryl amides to be synthesized, including several drug-like molecules.

Rhodium-Catalyzed Synthesis of Amides from Functionalized Blocked Isocyanates

Isocyanates are useful building blocks for the synthesis of amides, although their widespread use has been limited by their high reactivity, which often results in poor functional group tolerance and a propensity to oligomerize. Herein, a rhodium-catalyzed synthesis of amides is described coupling boroxines with blocked (masked) isocyanates. The success of the reaction hinges on the ability to form both the isocyanate and the organorhodium intermediates in situ. Relying on masked isocyanate precursors and on the high reactivity of the organorhodium intermediate results in broad functional group tolerance, including protic nucleophilic groups such as amines, anilines, and alcohols.

Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF3 Bond Cleavage

The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates. The control experiments show that the reaction proceeds via an isocyanate intermediate and/or alkoxide/amide dual anionic intermediate.

Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF3 Bond Cleavage

The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates. The control experiments show that the reaction proceeds via an isocyanate intermediate and/or alkoxide/amide dual anionic intermediate.

Chemoselective Synthesis of N-arylbenzamides and Benzoyloxyacetanilides from Aryl Isocyanides: Styrene as Aryl and Arylcarboxymethylene Source

Styrenes serve as unique aryl or arylcarboxymethylene source towards aryl isocyanides in the presence of Cu(II)/TBHP, and yield N-arylbenzamides or benzoyloxyacetanilides respectively. The chemoselectivity of the reaction is controlled by the nature of the substituents present on styrene ring. Whereas styrenes substituted with electron-releasing alkyl and alkoxy groups yield N-arylbenzamides, unsubstituted styrene and those with electron-withdrawing substituents furnish benzoyloxyacetanilides as the major product. With benzylamines as the substrate, N-arylbenzamides are formed exclusively as they act only as an aryl donor. TBHP serves as a promoter and oxygen source. Both the pathways are believed to proceed through an initial oxidative C?C bond cleavage of styrene. (Figure presented.).

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.

N-aryl secondary aryl amide synthetic method

The invention discloses an N-aryl secondary aryl amide synthetic method. The synthetic method is characterized in that arylboronic acid and aromatic primary amine, and a main catalyst and a cocatalystare added in a solvent, then the components are subjected to a carbonylation reaction and then separation and purification to obtain the N-aryl secondary aryl amide, and CO is introduced into a reaction system during a reaction process so that the pressure of the reaction system is 0.1-5 MPa. The synthetic method is concise and efficient, aromatic amine and organic boric acid and CO which are stable in air and easily available can be taken as the reaction raw materials, under existence of the solvent, the catalysts are added, and the secondary aryl amide is synthesized with high efficiency under mild reaction condition.

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.

A quick Chan-Lam C-N and C-S cross coupling at room temperature in the presence of square pyramidal [Cu(DMAP)4I]I as a catalyst

A rapid and efficient protocol for C-N and C-S cross coupling has been developed using a new square pyramidal copper complex, [Cu(DMAP)4I]I. The complex was successfully synthesized via a disproportionation reaction of CuI and DMAP in DMSO. The catalytic activity of the complex was found to be excellent for Chan-Lam coupling reaction between aryl boronic acid and amine, amide, azide or thiol. The reaction could be carried out in the presence of only 2 mol% of the copper catalyst in methanol at room temperature within a short time.

Hybrids of privileged structures benzothiazoles and pyrrolo[2,1-c] [1,4]benzodiazepin-5-one, and diversity-oriented synthesis of benzothiazoles

Privileged structures like Benzothiazole and Pyrrolobenzodiazepine offer wonderful opportunity to explore in anti-cancer drug discovery as a mean to counter drug-resistance problem. BT-PBD hybrids and diverse BT derivatives have been synthesized and their in vitro cytotoxic activities were screened against five cancer cell lines have been discussed. The novel compounds showed promising results as compared with the marketed drug etoposide and could well be used in future anti-cancer drug development studies.