53463-11-9

Upstream product

• 75-64-9 tert-butylamine 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 201230-82-2 carbon monoxide 
• 90-14-2 1-Iodonaphthalene 
• 119072-55-8 tert-butylisonitrile 
• 86-55-5 1-naphthalenecarboxylic acid 
• 13922-41-3 1-Naphthylboronic acid 
• 28912-93-8 1-naphthyldiazonium tetrafluoroborate 
• 66-77-3 1-naphthaldehyde 
• 4780-79-4 1-naphthalene methanol 
• 90-11-9 1-Bromonaphthalene 
• 90-12-0 1-Methylnaphthalene 
• 540-88-5 acetic acid tert-butyl ester 
• 86-53-3 1-Cyanonaphthalene 

Downstream Products

• 213318-25-3 C₂₂H₂₂⁽²⁾HNO 
• 1450753-73-7 N-tert-butyl-2-(4-nitrobenzamido)-1-naphthamide 

Relevant academic research and scientific papers

1,3,4,5-Tetrahydroazepin-2-ones by dearomatising anionic cyclisation of N-allyl-1-naphthamides

On treatment with t-BuLi and DMPU, 1-naphthamides bearing N-allyl or N- prenyl substituents cyclise to give a mixture of products from which seven- membered lactams can be isolated in up to 73% yield - the first example of an organolithium-C=C cyclisation leading to a seven-membered ring.

Nickel-catalyzed aminocarbonylation of Aryl/Alkenyl/Allyl (pseudo)halides with isocyanides and H2O

Herein described is a nickel-catalyzed aminocarbonylation of aryl/alkenyl/allyl (pseudo)halides with isocyanides, providing aryl/alkenyl/allyl amides in 41% to 92% yields. Functional groups such as F, Cl, OMe, and heteroaromatic rings are compatible in the reaction. A Ni(0)/Ni(II) catalytic cycle is proposed based on preliminary experiments and previous literature. The reaction features readily available nickel salt, broad functional group tolerance, and simple reaction conditions.

Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol

The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.

Pd(II)-Catalyzed Regioselective Multiple C-H Arylations of 1-Naphthamides with Cyclic Diaryliodonium Salts: One-Step Access to [4]- And [5]Carbohelicenes

Highly efficient and rapid construction of carbohelicenes is a desired but challenging task, especially starting from simple substrates. Herein, Pd(II)-catalyzed regioselective multiple C-H arylations of 1-naphthamides with cyclic diaryliodoniums have bee

Palladium/Copper-Catalyzed Oxidative Coupling of Arylboronic Acids with Isocyanides: Selective Routes to Amides and Diaryl Ketones

An efficient and alternative oxidative cross-coupling strategy starting from arylboronic acids and isocyanides for the selective synthesis of amides and diaryl ketones with palladium/copper catalysis is developed. Various substituted benzamides and benzop

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.

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.).

Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon

An unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst is disclosed. The experimental results and mechanistic study show that the isocyano group acts formally as an N1 synthon during the transformation, thus expanding the reactivity profile of isocyanide.

Practical synthesis of phthalimides and benzamides by a multicomponent reaction involving arynes, isocyanides, and CO2/H2O

Transition-metal-free multicomponent reactions involving arynes and isocyanides with either CO2 or H2O have been reported. With CO2 as the third component, the reactions resulted in the formation of N-substituted phthalimides. The utility of water as the third component furnished benzamide derivatives in moderate to good yields. These reactions took place under mild conditions with broad scope.

Ir(III)-catalyzed mild C-H amidation of arenes and alkenes: An efficient usage of acyl azides as the nitrogen source

Reported herein is the development of the Ir(III)-catalyzed direct C-H amidation of arenes and alkenes using acyl azides as the nitrogen source. This procedure utilizes an in situ generated cationic half-sandwich iridium complex as a catalyst. The reaction takes place under very mild conditions, and a broad range of sp2 C-H bonds of chelate group-containing arenes and olefins are smoothly amidated with acyl azides without the intervention of the Curtius rearrangement. Significantly, a wide range of reactants of aryl-, aliphatic-, and olefinic acyl azides were all efficiently amidated with high functional group tolerance. Using the developed approach, Z-enamides were readily accessed with a complete control of regio- and stereoselectivity. The developed direct amidation proceeds in the absence of external oxidants and releases molecular nitrogen as a single byproduct, thus offering an environmentally benign process with wide potential applications in organic synthesis and medicinal chemistry.