16770-34-6

Upstream product

• 1013-88-3 Benzophenone imine 
• 108-91-8 cyclohexylamine 
• 2051-90-3 Dichlorodiphenylmethane 
• 626-62-0 Cyclohexyl iodide 
• 1759-68-8 N-benzoylcyclohexylamine 
• 100-58-3 phenylmagnesium bromide 
• 5267-34-5 aminodiphenylmethane hydrochloride 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 110-82-7 cyclohexane 
• 931-53-3 Cyclohexyl isocyanide 
• 595-89-1 Tetraphenyllead 
• 18985-99-4 cyclohexylidene-N-(diphenylmethyl)amine 
• 91-00-9 Benzhydrylamine 

Downstream Products

• 574-45-8 N-(diphenylmethylidene)phenylamine 
• 1865-12-9 N-(diphenylmethyl)aniline 
• 735-11-5 N-(diphenylmethyl)cyclohexanamine 
• 108-91-8 cyclohexylamine 
• 119-61-9 benzophenone 
• 100-60-7 N-methylcyclohexylamine 

Relevant academic research and scientific papers

Copper(II)-Photocatalyzed N-H Alkylation with Alkanes

We report a practical method for the alkylation of N-H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)-H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N-H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.

Tandem Photoredox and Copper-Catalyzed Decarboxylative C(sp3)-N Coupling of Anilines and Imines Using an Organic Photocatalyst

An organic photoredox catalyst, 4CzIPN, was used in combination with a copper catalyst, CuCl, to effect decarboxylative C(sp3)-N coupling. The coupling worked with both anilines and imines as nitrogen sources and could be used to prepare a variety of alkyl amines from readily available alkyl carboxylic acids.

Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis

Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal-catalyzed cross-coupling of alkyl electrophiles with nitrogen nucleophiles. Described here is an approach to employ tandem photoredox and copper catalysis to enable the cross-coupling of alkyl N-hydroxyphthalimide esters, readily derived from alkyl carboxylic acids, with benzophenone-derived imines. Hydrolysis of the coupling products furnish alkylated primary amines. Primary, secondary, and tertiary alkyl groups can be transferred, and the coupling tolerates a diverse set of functional groups. The method allows rapid functionalization of natural products and drugs, and can be used to expedite syntheses of pharmaceuticals from readily available chemical feedstocks.

Benzhydrylamine: An effective aminating agent for the synthesis of primary amines

Aldehydes, ketones, alkyl toluene-p-sulfonates and halides are converted into the corresponding primary amines with benzhydrylamine as a valuable ammonia synthon in moderate to excellent yields.

Direct transformation of secondary amides into secondary amines: Triflic anhydride activated reductive alkylation

Versatile and mild: The first general method for the title transformation has been developed (see scheme; 2-F-Py=2-fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the r

Radical amination with trimethylstannylated benzophenone imine

Figure presented Intermolecular radical amination reactions of various primary, secondary, and tertiary alkyl radicals by using trimethylstannylated benzophenone imine A as a novel radical acceptor to provide imines of type B are described. These imines are readily reduced with NaBH4 to the corresponding secondary amines C. The novel radical amination can be combined with typical radical cyclization reactions.

Photoreduction of imines. An environmentally friendly approach to obtain amines

The photoreduction of different imines to amines in alcoholic solvents is reported. The reduction involves a versatile and chemoselective methodology that is environmentally friendly in that it avoids the use of metal hydrides and other dangerous reducing agents.