32047-93-1

Usage

InChI:InChI=1/C15H15NO2/c1-12(17)16(13-6-4-3-5-7-13)14-8-10-15(18-2)11-9-14/h3-11H,1-2H3

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 103-84-4 Acetanilid 
• 76154-08-0 (E)-N-(1-(4-methoxyphenyl)ethylidene)aniline 
• 696-62-8 para-iodoanisole 
• 62-53-3 aniline 
• 51-66-1 4-methoxyacetanilide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 1208-86-2 N-(4-methoxyphenyl)phenylamine 

Relevant academic research and scientific papers

SBA-15 Immobilized Phenanthroline-Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N-H Heterocycles with Aryl Halides

5-(N,N-bis-3-(triethoxysilyl) propyl) ureyl-1,10-phenanthroline was prepared and successively grafted onto mesoporous silica of SBA-15 to get SBA-15 anchored ligand which was then reacted with Cu(I) to get SBA-15 anchored complex as the heterogeneous copper catalyst. This catalyst was characterized by FT-IR, XRD, CHN, AAS, TGA, EDAX, BET, SEM and TEM. The activities of the catalyst were tested in C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. The catalyst showed high catalytic activities for these cross-coupling reactions providing good to excellent yields of desired products. Moreover, the catalyst can be easily recovered by simple filtration and reused several times without significant loss of its catalytic activity.

Metal-free n -arylation of secondary amides at room temperature

The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.

A simple copper-catalyzed synthesis of tertiary acyclic amides

The N-arylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper catalytic system. The corresponding tertiary acyclic amides, which can be found in numerous biologically active compounds, have been obtained in good to excellent yields.

A facile N-arylation of acetanilides with arynes

An efficient, mild and transition-metal-free method for the N-arylation of acetanilides, leading to a range of unsymmetrical diarylamine products is reported. Reactions of ortho-silylaryl triflates with acetanilides in the presence of tetrabutylammonium triphenyldifluorosilicate (TBAT) in toluene afforded the desired products in good to excellent yields. Regioselectivity was also observed when unsymmetrical aryne precursors were used.

Copper-catalyzed amidation of aryl iodides in the presence of various chelating ligands

N,N′-Dibenzylethylenediamine is presented as a new, efficient, and versatile bidentate ligand suitable for the copper catalyzed formation of the C-N bond. This bidentate ligand has been demonstrated to facilitate the copper catalyzed cross-coupling reactions of aryl iodides with amides to afford the desired products in good to excellent yields.

Amino acid-mediated Goldberg reactions between amides and aryl iodides

A highly general, experimentally simple, and inexpensive catalyst system was developed for the amidation of aryl iodides by using 5mol% of CuI as catalyst, 20mol% of an amino acid as ligand, and K3PO4 as base.

Copper-catalyzed amidation of aryl iodides using KF/Al2o 3: An improved protocol

A mild method for the copper-catalyzed amidation of aryl iodides is reported. This simple C-N bond forming procedure shows that the combination of air stable CuI and 1,10-phenanthroline in the presence of KF/Al 2O3 comprises an extremely efficient and general catalyst system for the N-amidation of aryl iodides. Different functionalized aryl iodides were efficiently coupled with amides using this method.

Oxidative rearrangement of ketimines to amides by MCPBA and BF3·OEt2

Several amides were obtained by an efficient method from the corresponding alkyl aryl ketimines in high yields. Ketimines are readily prepared from the corresponding ketones. This procedure involves the oxidation of alkyl aryl ketimines with MCPBA with BF3·OEt2. In this reaction, only aryl group of alkyl aryl ketimines was migrated to the electron deficient nitrogen atom.

New N- and O-arylations with phenylboronic acids and cupric acetate

A new method of arylating N-H and O-H containing compounds at room temperature with phenylboronic acids and cupric acetate in the presence of a tertiary amine promoter is described. Substrates include phenols, amines, anilines, amides, imides, ureas, carbamates, and sulfonamides.