10286-85-8

Usage

InChI:InChI=1/C13H10BrNO/c14-11-7-4-8-12(9-11)15-13(16)10-5-2-1-3-6-10/h1-9H,(H,15,16)

Upstream product

• 65-85-0 benzoic acid 
• 591-19-5 m-Bromoaniline 
• 108752-45-0 N-(3-bromophenyl)benzothioamide 
• 585-79-5 m-nitrobromobenzene 
• 100-51-6 benzyl alcohol 
• 63213-03-6 1,2-bis(3-bromophenyl)diazene 
• 201230-82-2 carbon monoxide 
• 98-80-6 phenylboronic acid 
• 2446-51-7 N-methoxybenzamide 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 95-14-7 1,2,3-Benzotriazole 
• 98-88-4 benzoyl chloride 
• 98-86-2 acetophenone 

Downstream Products

• 69918-19-0 5-bromo-2-phenylbenzo[d]oxazole 
• 305372-56-9 5-bromo-2-phenylbenzo[d]thiazole 
• 36247-07-1 7-bromo-2-phenylbenzo[d]thiazole 
• 77185-71-8 6-bromo-2-phenyl-1H-indole 
• 51774-35-7 N-(3-bromophenyl)-N-methylbenzamide 
• 1382354-11-1 2-(3-benzamidophenylamino)benzamide 
• 1382354-12-2 2-(3-N-methylbenzamidophenylamino)benzamide 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 23564-70-7 N-(o-Hydroxyphenol)benzamidine 

Relevant academic research and scientific papers

Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their anilides

A series of m- and p-substituted anilides of benzoic acid, 2-thienoic acid, and 2-furoic acid were prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shifts of proton and carbon signals of the acyl aromatic rings and the Hammett σ. Plots of the chemical shift values of the carbonyl carbons of the benzanilides against those of the 2-thienamides and 2-furamides gave an excellent correlation and the values of the slopes are 0.79 and 0.52, respectively, in dimethyl sulfoxide-d6. The slopes could be considered as a set of aromaticity index.

Peroxide-mediated direct synthesis of amides from aroyl surrogates

An efficient and metal-free method has been developed for the direct synthesis of amides from readily available azobenzenes reacting with aroyl surrogates such as alcohols, methylarenes. A variety of amides were afforded in moderate to good yields through this reaction. It is another example reported by our group for the use of azobenzene as the new radical acceptor.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride

A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Iron-catalyzed cross-coupling of N?methoxy amides and arylboronic acids for the synthesis of N-aryl amides

An efficient iron-catalyzed synthesis of N-aryl amides from N?methoxy amides and arylboronic acids is developed. FeCl3 is used as the sole catalyst for the cross-coupling reaction between N?methoxy amides and arylboronic acids without any other

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions

N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.

Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions

In this study, we investigate the amino and alkoxycarbonylation reaction between various substituted aryl halides, benzyl iodides, and iodocyclohexane with different types of amines and alcohols in the absence of carbon monoxide gas and ligands. Similar reactions are carried out at high temperatures, in the presence of appropriate ligands, stoichiometric amounts of bases, and gaseous carbon monoxide, which endanger the health of organic chemists. We present a novel method that does not utilize ligands, bases, gaseous CO, and special conditions. This procedure is a redox reaction carried out by new economic nano Ni/g-C3N4at room temperature and under visible light. Mo(CO)6was used toin situgenerate CO, to resolve the problems caused by the use of CO gas. This protocol has the ability to be used on a gram scale by using a continuous flow reactor.

Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant

An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.