53916-49-7

Upstream product

• 100-61-8 N-methylaniline 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 538-51-2 benzylidene phenylamine 
• 103-01-5 N-Phenylglycine 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 

Downstream Products

• 79188-13-9 (C₇H₈)Rh(NHC₆H₅CH₂CHC₆H₅NHC₆H₅)⁽¹⁺⁾*ClO₄^(1-)={RhC₇H₈NHC₆H₅CH₂CHC₆H₅NHC₆H₅}{ClO₄} 

Relevant academic research and scientific papers

Minimization of Back-Electron Transfer Enables the Elusive sp3 C?H Functionalization of Secondary Anilines

Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C?H functionalization.

Method for green synthesis of 1,2-diamine compound under catalysis of visible light

The invention discloses a method for green synthesis of a 1,2-diamine compound through visible light catalysis, and belongs to the technical field of organic synthesis. The method comprises the following steps: (1) adding N-phenylglycine or (4-fluorophenyl) glycine, a photocatalyst, an aldehyde compound or an imine compound, an arylamine compound and a solvent into a dry Schlenk tube; (2) sealingafter three times of air suction and exchange treatment; (3) carrying out stirring reaction under the irradiation of a Blue LED, and ending the reaction when TLC detects that the aldehyde compound disappears; and (4) adding water to quench, extracting with ethyl acetate, collecting an organic phase, drying with anhydrous sodium sulfate, filtering, adding silica gel, concentrating under reduced pressure, and purifying by column chromatography to obtain the diamine compound. Compared with the prior art, the method is simple in synthetic route, easily available in raw materials, simple and convenient to operate, environment-friendly, mild in reaction condition, good in reaction condition controllability and wide in substrate application range, and the preparation of the compound can realize an amplification reaction of gram level or above.

Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.