127598-85-0

Upstream product

• 106-49-0 p-toluidine 
• 1703-46-4 N,N-dimethyl-4-hydroxymethylaniline 
• 540-23-8 p-toluidine hydrochloride 
• 121-69-7 N,N-dimethyl-aniline 
• 17087-90-0 N-(4-dimethylaminobenzylidene)-p-toluidine 
• 1260501-57-2 C₁₆H₁₈N₂O 
• 100-10-7 4-dimethylamino-benzaldehyde 

Downstream Products

• 860751-44-6 N-(4-dimethylamino-benzyl)-N-p-tolyl-carbamonitrile 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 53477-27-3 4-<4-(N,N-Dimethylamino)benzyl>-N-methylaniline 
• 106-49-0 p-toluidine 
• 1555-67-5 N,N-di(2-cyanoethyl)-4-methylaniline 
• 400857-77-4 N'-(2,6-diisopropylphenyl)-N-[(4-dimethylaminophenyl)methyl]-N-(4-methylphenyl)urea 
• 83322-98-9 (4-amino-phenyl)-(4-dimethylamino-phenyl)-methane 

Relevant academic research and scientific papers

Five-Coordinate Low-Spin {FeNO}7 PNP Pincer Complexes

The synthesis and characterization of air-stable cationic mono nitrosonium Fe(I) PNP pincer complexes of the type [Fe(PNP)(NO)Cl]+ are described. These complexes are obtained via direct nitroslyation of [Fe(PNP)Cl2] with nitric oxide at ambient pressure. On the basis of magnetic and EPR measurements as well as DFT calculations, these compounds were found to adopt a low-spin d7 configuration and feature a nearly linear bound NO ligand suggesting FeINO+ rather than FeIINO? character. X-ray structures of all nitrosonium Fe(I) PNP complexes are presented. Preliminary investigations reveal that [Fe(PNPNH-iPr)(NO)(Cl)]+ efficiently catalyzes the conversion of primary alcohols and aromatic and benzylic amines to yield mono N-alkylated amines in good isolated yields.

Simple electrochemical reduction of nitrones to amines

The use of electricity allows the reduction of nitrones containing aromatic and heteroaromatic rings to the corresponding amines. The main advantage of this protocol relies on the fact that only electrons are needed, avoiding the use of different chemical

Manganese-Catalyzed Transfer Hydrogenation of Aldimines

The reduction of imines to amines via transfer hydrogenation was achieved promoted by phosphine-free manganese(I) catalyst. Using isopropanol as reductant, in the presence of tBuOK (4 mol %) and manganese complex [Mn(CO)3Br(κ2N,N-PyCH2NH2)] (2 mol %), a large variety of aldimines (30 examples) were typically reduced in 3 hours at 80 °C with good to excellent yield.

Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant

A one-pot two-step procedure was developed for the alkylation of amines via reductive amination of aldehydes using molecular dihydrogen as a reductant in the presence of a manganese pyridinyl-phosphine complex as a pre-catalyst. After the initial condensation step, the reduction of imines formed in situ is performed under mild conditions (50-100 °C) with 2 mol% of catalyst and 5 mol% of tBuOK under 50 bar of hydrogen. Excellent yields (>90%) were obtained for a large combination of aldehydes and amines (40 examples), including aliphatic aldehydes and amino-alcohols.

Air Stable Iron(II) PNP Pincer Complexes as Efficient Catalysts for the Selective Alkylation of Amines with Alcohols

A series of well-defined iron(II) complexes of the types [Fe(PNP)Br2] and [Fe(PNP)(CO)Br2] with PNP pincer ligands based on triazine and pyridine backbones were prepared and fully characterized. These complexes were tested as catalysts for the alkylation of amines by alcohols. The high-spin complexes [Fe(PNP)Br2] are catalytically inactive. The low-spin complexes [Fe(PNP)(CO)Br2] bearing a carbonyl co-ligand efficiently and selectively convert primary alcohols and aromatic and benzylic amines selectively into mono-N-alkylated amines in good to excellent isolated yields. A mechanistic proposal is given. (Figure presented.).

Divergent Coupling of Alcohols and Amines Catalyzed by Isoelectronic Hydride MnIand FeIIPNP Pincer Complexes

Herein, we describe an efficient coupling of alcohols and amines catalyzed by well-defined isoelectronic hydride MnIand FeIIcomplexes, which are stabilized by a PNP ligand based on the 2,6-diaminopyridine scaffold. This reaction is an environmentally benign process implementing inexpensive, earth-abundant non-precious metal catalysts, and is based on the acceptorless alcohol dehydrogenation concept. A range of alcohols and amines including both aromatic and aliphatic substrates were efficiently converted in good to excellent isolated yields. Although in the case of Mn selectively imines were obtained, with Fe—exclusively monoalkylated amines were formed. These reactions proceed under base-free conditions and required the addition of molecular sieves.

Co(II) PCP Pincer Complexes as Catalysts for the Alkylation of Aromatic Amines with Primary Alcohols

Efficient alkylations of amines by alcohols catalyzed by well-defined Co(II) complexes are described that are stabilized by a PCP ligand (N,N′-bis(diisopropylphosphino)-N,N′-dimethyl-1,3-diaminobenzene) based on the 1,3-diaminobenzene scaffold. This reaction is an environmentally benign process implementing inexpensive, earth-abundant nonprecious metal catalysts and is based on the acceptorless alcohol dehydrogenation concept. A range of primary alcohols and aromatic amines were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields.

A Highly Efficient Base-Metal Catalyst: Chemoselective Reduction of Imines to Amines Using An Abnormal-NHC-Fe(0) Complex

A base-metal, Fe(0)-catalyzed hydrosilylation of imines to obtain amines is reported here which outperforms its noble-metal congeners with the highest TON of 17000. The catalyst, (aNHC)Fe(CO)4, works under very mild conditions, with extremely low catalyst loading (down to 0.005 mol %), and exhibits excellent chemoselectivity. The facile nature of the imine reduction under mild conditions has been further demonstrated by reducing imines towards expensive commercial amines and biologically important N-alkylated sugars, which are difficult to achieve otherwise. A mechanistic pathway and the source of chemoselectivity for imine hydrosilylation have been proposed on the basis of the well-defined catalyst and isolable intermediates along the catalytic cycle.

Cyclopentadienyl N-heterocyclic carbene-nickel complexes as efficient pre-catalysts for the hydrosilylation of imines

The in situ generated nickel hydride complex, [Ni(Mes2NHC)HCp], and its cationic analogue, [Ni(Mes2NHC)(NCMe)Cp](PF6), are efficient and chemoselective pre-catalysts for the hydrosilylation of both aldimines and ketimines under mild conditions. The Royal Society of Chemistry.

NHC-carbene cyclopentadienyl iron based catalyst for a general and efficient hydrosilylation of imines

A general and efficient hydrosilylation of imines catalysed by a well defined NHC-carbene cyclopentadienyl iron complex has been developed. Both aldimines and ketimines are converted to the corresponding amines under mild conditions, and under visible light activation.