107455-66-3

Upstream product

• 3230-51-1 p-hydroxybenzal-p-toluidine 
• 106-49-0 p-toluidine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 2101-86-2 p-methylazidobenzene 
• 6554-98-9 trans-4-Hydroxystilbene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 107917-24-8 4-(N-Nitroso-p-toluidinomethyl)-phenol 

Relevant academic research and scientific papers

Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds

A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

An Efficient Metal-Free Method for the Denitrosation of Aryl N-Nitrosamines at Room Temperature

A simple and practical method for the denitrosation of aryl N-nitrosamines to secondary amines is reported under metal-free conditions using iodine and triethylsilane. Several reduction-susceptible functional groups such as alkene, alkyne, nitrile, nitro, aldehyde, ketone and ester were found to be very stable during the denitrosation, which is remarkable. Broad substrate scope, room temperature reactions and excellent yields are the additional features of the current methodology. (Figure presented.).

A one-pot synthesis of N-alkylaminobenzenes from nitroaromatics: reduction followed by reductive amination using B10H14

N-Alkylaminobenzenes were prepared in a simple and efficient one-pot synthesis by reduction of nitrobenzenes followed by reductive amination with decaborane (B10H14) in the presence of 10% Pd/C.