28386-83-6

Upstream product

• 103-71-9 phenyl isocyanate 
• 122-39-4 diphenylamine 
• 98-80-6 phenylboronic acid 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 66003-76-7 Diphenyliodonium triflate 
• 5663-04-7 N,N,N'-triphenylurea 

Relevant academic research and scientific papers

Metal-Free Oxidative C-H Amidation of N,N′-Diarylureas with PhI(OAc)2: Synthesis of Benzimidazol-2-one Derivatives

Benzimidazol-2-ones have various biological functions and are usually prepared by reactions of substituted benzene-1,2-diamines with carbonyl-containing compounds or intramolecular N-arylations using substrates with carbon-halogen bonds. However, the star

Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system

A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.

Metal-free regioselective formation of C-N and C-O bonds with the utilization of diaryliodonium salts in water: Facile synthesis of: N-Arylquinolones and aryloxyquinolines

Regioselective construction of crucial C-N and C-O bonds leading to N-Arylquinolones and aryloxyquinolines has been accomplished by employing easily accessible diaryliodonium salts and quinolones in water under metal-and ligand-free conditions. This opera

Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates

A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.