76570-50-8

Upstream product

• 58377-40-5 tert-butyl N-hydroxy-N-phenylcarbamate 
• 77-78-1 dimethyl sulfate 
• 1483-73-4 diphenyliodonium bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58377-44-9 N-(tert-butoxycarbonyl)-O-methylhydroxylamine 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 100-65-2 N-Phenylhydroxylamine 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 122019-30-1 C₆H₁₂ClNO₃ 
• 71-43-2 benzene 

Relevant academic research and scientific papers

Cesium Carbonate Promoted Direct Arylation of Hydroxylamines and Oximes with Diaryliodonium Salts

A transition-metal-free approach for the arylation of hydroxylamines and oximes with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of cesium carbonate. As a result, a wide range of N- and O-arylate

Palladium-catalyzed coupling of hydroxylamines with aryl bromides, chlorides, and iodides

The bis-pyrazole phosphine ligand BippyPhos is effective for the palladium-catalyzed cross-coupling of hydroxylamines with aryl bromides, chlorides, and iodides. Reactions proceed smoothly at 80 °C in toluene in the presence of Cs2CO3/sub

Copper-catalyzed coupling of hydroxylamines with aryl iodides

An efficient method for the copper-catalyzed N-arylation of hydroxylamines with aryl iodides is described. A variety of N- and O-functionalized hydroxylamines were transformed in good to excellent yield with a broad range of aryl coupling partners. Methods for the selective deprotection of either the N- or O-substituents for further functionalization are also described.

An Electrophilic Aromatic Substitution by N-Methoxyamides via Hypervalen Iodine Intermediates

Treatment of N-methoxyamides with hypervalent iodine compounds generates electron deficient nitrogen species which react intra- or intermolecularly with an aromatic group to give N-aryl-N-methoxyamides in good yields.

Electrophilic Aromatic Substitution with N-Methoxy-N-acylnitrenium Ions Generated from N-Chloro-N-methoxyamides: Syntheses of Nitrogen Heterocyclic Compounds Bearing a N-Methoxyamide Group

N-Methoxy-N-acylnitrenium ions (II), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N-methoxyamides in good yields.In the case of the intramolecular cyclization of N-chloro-N-methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups.Nitrenium ions II can primarily attack three positions (C-1, C-2, and C-6) of a phenyl ring.Normally II attack C-6.On the other hand, when the ortho position was occupied with a substituent group, II attacked both C-2 and C-6, in the former case followed by a 1,2-substituent migration, which was proved by a deuterium labeling experiment.Especially, when a methoxy group is substituted on ortho or para position, II attack C-1 due to the effect of the electron-releasing methoxy group to give spiro dienone compounds 39.A general discussion of the utility and mechanistic details of these reactions is presented.

Studies on the Preparation of N-Alkyl-O-phenylhydroxylamines

Several possible routes to the title compounds have been investigated.The reaction of N-hydroxycarbamates (1) with diphenyliodonium bromide gave, unexpectedly, N-hydroxy-N-phenylcarbamates (2), while N-methyl-N-hydroxycarbamates (6) gave 2-(N-methyl-N-alkoxycarbonylamino)phenols (7).Mechanistic aspects of the N-arylations and subsequent rearrangements are discussed.The desired N-alkyl-O-phenylhydroxylamines were obtained by the reduction of O-phenyloximes (15) with sodium cyanoborohydride.