25069-88-9

Upstream product

• 273-53-0 benzoxazole 
• 591-50-4 iodobenzene 
• 95-55-6 2-amino-phenol 
• 108-86-1 bromobenzene 
• 644-71-3 2-(phenylamino)phenol 
• 88-75-5 2-hydroxynitrobenzene 

Downstream Products

• 1150-62-5 N-phenylcarbazole 

Relevant academic research and scientific papers

COMPOUND WHICH INHIBITS TELOMERE-BINDING PROTEIN, AND TELOMERE-BINDING PROTEIN INHIBITOR CONTAINING SAME

The compound according to the present invention is a compound represented by the following chemical formula: wherein, in the above-described chemical formula, R1 is oxygen or sulfur, and R2 to R6 are each independently sel

8-exo-dig-Selective Cycloisomerization for the Synthesis of Dibenzo[b,e][1,4]diazocines Using Cationic AuI Catalysts

The cationic AuI-catalyzed intramolecular reaction of N-propargyl-2-anilinoanilines gave a diazocine skeleton via 8-exo-dig-selective cycloisomerization by the suppression of 6-endo-dig cycloisomerization. Both terminal and internal alkynes could be used according to the choice of ligand of the AuI complex, and various dibenzo[b,e][1,4]diazocines were obtained. Control experiments suggested that two nitrogen atoms in the tether of substrates were critical in this selective transformation.

Synthesis of N-Arylcarbazoles by Palladium-Catalyzed Direct C–H Arylation of 2-(Diarylamino)phenyl Triflates

The palladium-catalyzed direct arylation of a series of 2-(diarylamino)phenyl triflates was examined. The triflates were first synthesized in moderate to good yields through the CuI-catalyzed aryl amination of aminophenol and aryl iodides, followed by triflation of the resulting triarylphenols. The thus-obtained 2-(diarylamino)phenyl triflates were subjected to direct C–H arylation under Pd catalysis to furnish the corresponding N-arylcarbazoles in excellent yields if Josiphos was used as the supporting ligand.

Synthesis of triphenylamines: Via ligand-free selective ring-opening of benzoxazoles or benzothiazoles under superparamagnetic nanoparticle catalysis

CuFe2O4 superparamagnetic nanoparticles were utilized as an effective recyclable heterogeneous catalyst for the synthesis of triphenylamines via the ligand-free selective ring-opening reaction of benzoxazoles or benzothiazoles with iodoarenes. The nano CuFe2O4 demonstrated noticeably higher catalytic efficiency than a series of homogeneous catalysts and heterogeneous catalysts. It was possible to separate the nano CuFe2O4 by using a magnet, and the recovered catalyst was reused many times while its activity could be maintained. To the best of our knowledge, this is the first example of heterogeneous catalysis for the transformation of benzoxazoles, and the transformation of benzothiazoles to triphenylamines has not been previously reported in the literature.

Ligand-Free, Cu- and Fe-Catalyzed Selective Ring-Opening Arylations of Benzoxazoles with Aryl Iodides

Cu- or Fe-based catalyst systems have been reported to selectively catalyze the N,N-diarylation or N-monoarylation of benzoxazoles ring-opening with aryl iodides in the absence of additional added ligand in polyethylene glycol under an inert atmosphere. Two types of coupling products (triphenylamines and diphenylamines) have been examined and the reaction routes can be simply controlled by changing the metal salts (Cu or Fe) as catalyst. A range of substrates have been investigated for the diverse reactions, and the corresponding arylation products were achieved in good to high yields. This selective, low-cost, and environmentally friendly protocol displays great potential for replacing existing methodologies as well as extending the synthetic applications of benzoxazoles.

Copper-catalyzed selective arylations of benzoxazoles with aryl iodides

A copper-catalyzed direct ring-opening double N-arylation of benzoxazoles with aryl iodides has been developed. The present system exhibits high selectivity despite competition from C-arylation. The selectivity between ring-opening N-arylation and C-arylation was controlled by the choice of reaction vessel. The nitrile bound bis(triphenylphosphine)copper cyanide was identified as the active catalytic species for both reactions, and when combined with a nitrile-containing solvent, enhanced the reaction efficiency.

A general route for synthesis of N-aryl phenoxazines via copper(i)-catalyzed N-, N-, and O-arylations of 2-aminophenols

A novel copper(i)-catalyzed tandem reaction of N- and O-arylations of 2-[N-(2-chlorophenyl)amino]phenols was developed, by which a series of structurally novel N-aryl phenoxazines were synthesized efficiently. This success owes much to the discovery of hi

Copper-catalyzed direct synthesis of di- and triphenylamines: A dramatic accelerating effect of 2-aminophenols

Utilizing the dramatic accelerating effect of 2-aminophenols, we developed a copper-catalyzed system for the selective synthesis of di- and triphenylamines. In addition, N- and O-arylation could be achieved in coupling reactions between 2-aminophenol and nitroaryl halides. A copper-catalyzed system for the selective synthesis of di- and triphenylamines has been developed. This new protocol provides a direct and efficient way to synthesize o-hydroxy-substituted di- and triphenylamines. Copyright

Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols

O- or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates. We have developed a complementary set of Cu- and Pd-based catalyst systems for the selective O- and N-arylation of unprotected aminophenols using aryl halides. Selective O-arylation of 3- and 4-aminophenols is achieved with copper-catalyzed methods employing picolinic acid or CyDMEDA, trans-N,N′-dimethyl-1,2- cyclohexanediamine, respectively, as the ligand. The selective formation of N-arylated products of 3- and 4-aminophenols can be obtained with BrettPhos precatalyst, a biarylmonophosphine-based palladium catalyst. 2-Aminophenol can be selectively N-arylated with CuI, although no system for the selective O-arylation could be found. Coupling partners with diverse electronic properties and a variety of functional groups can be selectively transformed under these conditions.

1,2,3,4-Tetrahydro-8-hydroxyquinoline-promoted copper-catalyzed coupling of nitrogen nucleophiles and aryl bromides

(Chemical Equation Presented) Based on the dramatic accelerating effect of 2-aminophenol, three ligands derived from 2-aminophenol were developed. Copper-catalyzed coupling reaction of nitrogen-containing nucleophiles with aryl bromides was efficiently carried out under mild conditions using 1,2,3,4-tetrahydro-8-hydroxyquinoline as a novel, simple, and versatile ligand.