80143-73-3

Upstream product

• 371-40-4 4-fluoroaniline 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 39769-09-0 4-fluoro-N-[(1E/Z)-(4-fluorophenyl)methylene]aniline 
• 164362-62-3 1,2-bis(4-fluorophenyl)-4-methylenepyrrolidine 

Downstream Products

• 75137-18-7 N-(4-Fluoro-benzyl)-N-(4-fluoro-phenyl)-benzenesulfonamide 

Relevant academic research and scientific papers

Metal-Ligand Cooperation Facilitates Bond Activation and Catalytic Hydrogenation with Zinc Pincer Complexes

A series of PNP zinc pincer complexes capable of bond activation via aromatization/dearomatization metal-ligand cooperation (MLC) were prepared and characterized. Reversible heterolytic N-H and H-H bond activation by MLC is shown, in which hemilability of the phosphorus linkers plays a key role. Utilizing this zinc pincer system, base-free catalytic hydrogenation of imines and ketones is demonstrated. A detailed mechanistic study supported by computation implicates the key role of MLC in facilitating effective catalysis. This approach offers a new strategy for (de)hydrogenation and other catalytic transformations mediated by zinc and other main group metals.

Conversion of aldimines to secondary amines using iron-catalysed hydrosilylation

Iron-catalyzed hydrosilylation of imines to amines using a well-defined iron complex is reported. This method employs relatively mild conditions, by reaction of imine, (EtO)3SiH in a 1 : 2 ratio in the presence of 1 mol% precatalyst ([BIAN]Fe(η6-toluene), 3, BIAN = bis(2,6-diisopropylaniline)acenaphthene) at 70 °C. A broad scope of imines was readily converted into the corresponding secondary amines without the need for precatalyst activators.

Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts

CdSe/CdS core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radical. This precious metal free transformation is easy to scale up and can be carried out by a one-pot protocol directly from aldehyde, amine, and thiophenol. Additional advantageous features of this protocol include a wide substrate scope, high yield of the amine products, extremely low catalyst loading (0.001 mol %), high turnover number (105), and the mild reaction conditions of using visible light or sun light at room temperature in neutral media.

Synthesis of N-benzyl-N-phenylthiophene-2-carboxamide analogues as a novel class of enterovirus 71 inhibitors

A series of novel human enterovirus 71 inhibitors, N-benzyl-N-phenylthiophene-2-carboxamide analogues, were synthesized and their antiviral activities were evaluated in vitro. Most derivatives of this structure against EV71 had a low micromolar range in the RD (rhabdomyosarcoma) cell lines. The most potent compound 5a, N-(4-bromobenzyl)-N-(4-fluorophenyl)thiophene-2-carboxamide, showed low micromolar activity against EV71 (EC50 = 1.42 μM) compared to the reference anti-EV71 drug enviroxime (EC50 = 0.15 μM). Preliminary SAR studies revealed that the thiophene-2-carboxamide core is crucial for maintaining antiviral activity, and N-substituent phenyl groups largely influenced the anti-EV71 efficacy of this new class of potent antiviral agents.

Ruthenium(II) complexes containing lutidine-derived pincer CNC ligands: Synthesis, structure, and catalytic hydrogenation of C=N bonds

Abstract A series of Ru complexes containing lutidine-derived pincer CNC ligands have been prepared by transmetalation with the corresponding silver-carbene derivatives. Characterization of these derivatives shows both mer and fac coordination of the CNC ligands depending on the wingtips of the N-heterocyclic carbene fragments. In the presence of tBuOK, the Ru-CNC complexes are active in the hydrogenation of a series of imines. In addition, these complexes catalyze the reversible hydrogenation of phenantridine. Detailed NMR spectroscopic studies have shown the capability of the CNC ligand to be deprotonated and get involved in ligand-assisted activation of dihydrogen. More interestingly, upon deprotonation, the Ru-CNC complex 5e(BF4) is able to add aldimines to the metal-ligand framework to yield an amido complex. Finally, investigation of the mechanism of the hydrogenation of imines has been carried out by means of DFT calculations. The calculated mechanism involves outer-sphere stepwise hydrogen transfer to the C=N bond assisted either by the pincer ligand or a second coordinated H2 molecule. The outer limits: Facially coordinated Ru-CNC complexes, in the presence of tBuOK, are active catalysts in the hydrogenation of a series of substrates containing C=N bonds (see scheme). Intermediate species in the catalytic cycle have been studied by using NMR spectroscopy; DFT calculations support a stepwise outer-sphere mechanism for the hydrogen transfer to the C=N bond assisted by either the pincer ligand or a second coordinated H2 molecule.

N-Alkylation of amines through hydrogen borrowing over a heterogeneous Cu catalyst

Substitution of alkylhalides for the synthesis of amines is a relevant target for synthetic chemists. Secondary amines can be obtained in a one pot-one step reaction from secondary and benzylic alcohols and aniline over a heterogeneous copper catalyst. The process does not require any additive, is intrinsically safe and produces no waste.

A metal nanoparticle-based supramolecular approach for aqueous biphasic reactions

β-cyclodextrin immobilized on Pd nanoparticles was successfully employed as an efficient phase-transfer catalyst in aqueous biphasic hydrogenation reactions. The Royal Society of Chemistry 2005.

1-SUBSTITUTED-2-(N-PHENYL-N-(PHENYL-METHYL)METHANAMINE)-4,5-DIHYDRO-IMIDAZOLES AND RELATED COMPOUNDS AND THEIR USE IN TREATING CALCIUM OVERLOAD IN BRAIN CELLS

The present patent application discloses compounds of the formula STR1 wherein R 1 is C 1-10 saturated or unsaturated alkyl; or STR2 wherein R'" is H or STR3 R 2 is phenyl which is unsubstituted or substituted one or more times with halogen, CF 3, C. sub.1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; benzyl which may be substituted one or more times with halogen, CF 3, C 1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; pyridyl; or cyclohexyl;R 3 phenyl which is unsubstituted or substituted one or more times with halogen, CF 3, C 1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; naphthyl which may be substituted one or more times with halogen, CF 3, C 1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; pyridyl; C 1-6 unsaturated alkyl; furanyl;R 4 is H, C 1-6-alkyl, or benzyl; or STR4 together form STR5 R' and R" are each hydrogen or together form an extra benzo ring; and wherein the dotted line represents an optional extra bond between the two carbon atoms designated α and β, or a pharmaceutically-acceptable addition salt thereof.The compounds are useful as pharmaceuticals, for example in the treatment of Ca overload in brain cells. "

Imidazole derivatives as calcium channel blockers

The present patent application discloses compounds of the formula ψψ ψwhereinψ R1 is C1-10-alkyl which may be branched; C1-10-unsaturated alkyl; or CHR'''''' ψψ ψwherein R'''''' is H or ψψ ψRy is phenyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; benzyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; pyridyl; or cyclohexyl;ψ R3 phenyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; naphthyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; pyridyl; C1-6 unsaturated alkyl; furanyl;ψ R4 is H, C1-6-alkyl, or benzyl;ψ or ψψ ψtogether form ψψ ψR5 is H, or C1-6-alkyl;ψ R'' and R'''' are each hydrogen or together form an extra benzo ring;ψ and wherein the dotted line represents an optional extra bond between the two carbon atoms designated à and á, or a pharmaceutically-acceptable addition salt thereof. ψThe compounds are useful as pharmaceuticals, for example in the treatment of Ca overload in brain cells.ψ