53595-99-6

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 95-51-2 o-chloroaniline 
• 95-57-8 2-monochlorophenol 
• 104-94-9 4-methoxy-aniline 
• 5720-07-0 4-methoxyphenylboronic acid 
• 88-73-3 2-Chloronitrobenzene 

Downstream Products

• 1257334-80-7 4-(2-chlorophenylimino)cyclohexa-2,5-dienone 
• 18992-85-3 3-methoxycarbazole 
• 501326-35-8 N-benzyl-2-chloro-N-(4-methoxyphenyl)aniline 

Relevant academic research and scientific papers

Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature

We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.

Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride

While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included.

A facile C-N bond formation: One-pot reaction of phenols and amines via smiles rearrangement

Diarylamines and arylalkylamines were synthesized in high yields from 2-chlorophenols and amines, activated by chloroacetyl chloride under microwave irradiation (20-60 min) or conventional thermal conditions (3-6 h). The key transformation is believed to

Process for preparing arylamines

The invention relates to a process for preparing arylamines or heteroarylamines or arylamides or heteroarylamides by cross-coupling of primary or secondary amines or amides with substituted aryl or heteroaryl compounds in the presence of a Br?nsted base a

A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation

Sequential palladium catalysed amination and C-H activation reactions occur between 2-chloro-N-alkylated anilines and aryl bromides to give carbazoles in one pot.

Process for the manufacture of fluoran compounds

A process for the preparation of a fluoran compound of the formula STR1 wherein R, R1, R2 and R4 are each independently hydrogen, halogen, lower alkyl or lower alkoxy, R3 is hydrogen, halogen, lower alkyl, lower alkoxy or --NX3 X4, or (R1 and R2) or (R3 and R4) each pair together with the carbon atoms to which they are attached, form a fused benzene nucleus, X1, X2, X3 and X4 are each independently hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by cyano, halogen, hydroxy, tetrahydrofuryl or lower alkoxy, or are cycloalkyl, aryl or aralkyl or (X1 and X2) or (X3 and X4) are each independently together with the nitrogen to which are attached a 5- or 6-membered heterocyclic ring, and the ring A is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkylthio, lower alkoxy, lower alkoxycarbonyl, amino, mono-lower alkylamino, di-lower alkylamino or lower alkyl carbonylamino, which process comprises (1) reacting a ketonic acid of the formula STR2 with a substituted phenol derivative of the formula STR3 wherein Z is hydrogen, lower alkyl, formyl or lower alkanoyl and A, R, R1, R2, R3, R4, X1 and X2 have the given meanings, (2) adding the reaction product to an aqueous-organic liquor containing a non-polar organic solvent and a base at a temperature of 50° to 90° C., (3) separating the organic phase and (4) removing the organic solvent to obtain the fluoran of the formula (1).