80192-95-6

Upstream product

• 100-61-8 N-methylaniline 
• 2243-83-6 2-naphthaloyl chloride 
• 93-09-4 naphthalene-2-carboxylate 
• 1037-25-8 O-(2-naphthyl) N-methyl-N-phenyl thiocarbamate 
• 10506-37-3 O-2-naphthalenyl-carbonochloridothioate 
• 135-19-3 β-naphthol 
• 201230-82-2 carbon monoxide 
• 612-55-5 2-iodonaphthalene 
• 2459-25-8 methyl naphthalene-2-carboxylate 
• 130576-52-2 N-(2-naphthoyl) saccharin 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 327053-57-6 N-(3-(trifluoromethyl)phenyl)-2-naphthamide 
• 70021-83-9 N-phenyl-2-naphthamide 
• 93-09-4 naphthalene-2-carboxylate 

Relevant academic research and scientific papers

Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N -Acylsaccharins

The use of tertiary amines as surrogates for secondary amines has prominent advantages in terms of stabilization and ease of handling. A Ni-catalyzed transamidation of N -acylsaccharins with tertiary aromatic amines is reported. By using tert -butyl hydroperoxide as the terminal oxidant, this reaction permits selective cleavage of the C(sp 3)-N bonds of unsymmetrical tertiary aromatic amines depending on the sizes of the alkyl substituents.

KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines: Synthesis of amides and sulfonamides

KMnO4-mediated oxidative C[sbnd]N bond cleavage of tertiary amines producing secondary amine was introduced, which was trapped by electrophiles (acyl chloride and sulfonyl chloride) to form amides and sulfonamides. The reaction could take place at mild condition, tolerating a wide range of function groups and affording products in moderate to excellent yields.

Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters

We report the first catalytic method for activating the acyl C-O bonds of methyl esters through an oxidative-addition process. The oxidative-addition adducts, formed using nickel catalysis, undergo in situ trapping to provide anilide products. DFT calculations are used to support the proposed reaction mechanism, to understand why decarbonylation does not occur competitively, and to elucidate the beneficial role of the substrate structure and the Al(OtBu)3 additive on the kinetics and thermodynamics of the reaction.

Palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines

A novel and efficient palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of a variety of valuable imides and tertiary benzanilides under an atmospheric pressure of CO. Copyright

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.

The conversion of carboxylic acids into amides via NCS/triphenylphosphine

Amides can be generated in very high yields under mild conditions from the corresponding carboxylic acid and amine in the presence of equivalent amounts of triphenylphosphine and N-halosuccinimides, e.g., NCS or NBS.