10222-93-2

Upstream product

• 119072-55-8 tert-butylisonitrile 
• 121-92-6 3-nitrobenzoic acid 
• 121-90-4 m-nitrobenzoic acid chloride 
• 619-24-9 3-nitrobenzonitrile 
• 75-65-0 tert-butyl alcohol 
• 645-00-1 m-iodonitrobenzene 
• 99-09-2 3-nitro-aniline 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 
• 585-79-5 m-nitrobromobenzene 
• 540-88-5 acetic acid tert-butyl ester 
• 201230-82-2 carbon monoxide 
• 75-64-9 tert-butylamine 

Downstream Products

• 645-09-0 3-nitrobenzamide 

Relevant academic research and scientific papers

The copper-catalyzed cross-coupling reactions of aryl diazonium salts and isocyanides

The copper-catalyzed cross-coupling reaction of aryl diazonium salts and isocyanides has been performed. This is a successful example of preparation of arylcarboxyamides with moderate to good yield under mild conditions.

Facile synthesis of primary amides and ketoamides via a palladium-catalysed carbonylation-deprotection reaction sequence

Various primary amides and ketoamides have been obtained in good yields in a two-step reaction sequence. The first step involves the synthesis of aryl/alkenyl N-tert-butyl amides and aryl N-tert-butyl ketoamides from the corresponding iodides via palladium-catalysed carbonylation in the presence of t-BuNH2 as the nucleophile. Carbonylation was followed by selective cleavage of the t-Bu group using TBDMSOTf as the reagent.

A novel approach for the synthesis of aryl amides

A novel and highly efficient approach for the synthesis of aryl amides in high yields by the reaction of carboxylic acids and isocyanides in methanol at ambient temperature is reported.

KAl(SO4)2.12H2O as an eco-friendly and reusable catalyst for the synthesis of amides by the Ritter reaction

KAl(SO4)2.12H2O (Alum) is an eco-friendly, inexpensive, readily available and reusable and was applied as catalyst to the synthesis of N-alkyl amides from nitriles and alcohols by the Ritter reaction. This solvent-free procedure is very simple with excellent yields and easy work-up.

One-pot synthesis of N-tert-butyl amides from alcohols, ethers and esters using ZnCl2/SiO2 as a recyclable heterogeneous catalyst

ZnCl2/SiO2 has been found to be an efficient and reusable catalyst for conversion of alcohols, ethers and esters to corresponding amides via the Ritter reaction in high yield. It was found that benzonitrile reacted with tert-butyl acetate faster than the other sources of tert-butyl carbocation.

Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

A Visible-Light-Driven, Metal-free Route to Aromatic Amides via Radical Arylation of Isonitriles

The photochemical metal-free carboamidation of aryl radicals has been exploited for the preparation of aromatic amides, including hetero- and polyaromatic derivatives, under visible light irradiation of arylazo sulfones in the presence of isocyanides in aqueous acetonitrile. The process was useful for the smooth preparation of the antidepressant moclobemide. (Figure presented.).

Cp?CoIII-Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Hydroarylation of internal alkynes by cost-effective CoIII-catalysis, directed by N-tert-butyl amides, is achieved to avail mono- or dihydroarylated amide products selectively in an atom and step economic way. Several important functional groups were tolerated under the reaction conditions, and syn-hydroarylation products were exclusively isolated. Notably, a 4-fold C-H hydroarylation provided a highly conjugated organic framework in one step. Kinetic study with extensive deuterium labeling experiments were performed to support the proposed mechanism.

Amidation of aryl halides with isocyanides using a polymer-supported palladium-n-heterocyclic carbene complex as an efficient, phosphine-free and heterogeneous recyclable catalyst

The amidation of aryl halides with alkyl/aryl isocyanides to give the corresponding amides using polymer-supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous recyclable catalyst is described. The catalytic system was optimized with respect to various reaction parameters giving excellent yields of the desired products. The catalyst can be easily separated by a simple filtration process and recycled further for up to four consecutive recycle without any loss of activity and selectivity. The protocol is advantageous due to the ease in handling of the catalyst, simple workup procedure, phosphine-free, and effective catalyst recyclability. Georg Thieme Verlag Stuttgart New York.

A transition-metal-free synthesis of arylcarboxyamides from aryl diazonium salts and isocyanides

A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, has been developed. This novel conversion was initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation, affording the corresponding arylcarboxyamide upon hydration of the nitrilium intermediate.