40625-28-3

Upstream product

• 765-50-4 2-Chloromethylthiophene 
• 62-53-3 aniline 
• 98-03-3 thiophene-2-carbaldehyde 
• 51305-92-1 cyclohexyl-thiophen-2-ylmethylene-amine 
• 5918-68-3 (E)-N-phenyl-1-(thiophen-2-yl)methanimine 
• 473929-75-8 phenyl-thiophen-2-ylmethyl-triethylsilanyl-amine 
• 98-95-3 nitrobenzene 
• 636-72-6 2-thiophenemethanol 
• 1918-82-7 2-vinylthiophene 
• 81994-43-6 2-(phenylamino)-2-(thiophen-2-yl)acetonitrile 
• 5918-68-3 N-thiophen-2-ylmethyleneaniline 
• 6846-13-5 N-phenyl-2-thiophenecarboxamide 
• 1527-91-9 N-phenylbenzamidine 

Downstream Products

• 117776-22-4 2-Brom-N-(2-thienylmethyl)acetanilid 
• 439908-95-9 1-methyl-3(R)-(phenyl(thiophen-2-ylmethyl)carbamoyloxy)-1-azoniabicyclo[2.2.2]octane bromide 
• 439909-09-8 1-(2-phenoxyethyl)-3-(R)-(phenyl)(thiophen-2-ylmethyl)carbamoyloxy-1-azoniabicyclo[2.2.2]octane bromide 
• 439908-94-8 phenyl(thiophen-2-ylmethyl)carbamic acid 1-azabicyclo[2.2.2]oct-3(R)-yl ester 
• 1312718-58-3 C₁₂H₁₀ClNOS 
• 1374762-46-5 N-phenyl-N-(thiophen-2-ylmethyl)-2-(m-tolyloxy)acetamide 
• 34243-33-9 2-thiophen-2-yl-quinoline 
• 81994-43-6 2-(phenylamino)-2-(thiophen-2-yl)acetonitrile 
• 6846-13-5 N-phenyl-2-thiophenecarboxamide 
• 1374762-27-2 2-(benzo[d][1,3]dioxol-5-yloxy)-N-phenyl-N-(thiophen-2-ylmethyl)acetamide 
• 936215-79-1 dichlorobis-κ-N-[N-(2-thienylmetyl)-aniline]palladium(II) 
• 122335-41-5 1-ethyl-1-[2-(phenyl-[2]thienylmethyl-carbamoyloxy)-ethyl]-pyrrolidinium; iodide 

Relevant academic research and scientific papers

Reactions of cyclometalated carbonyliron complex derived from thienyl Schiff base

Cyclometalated hexacarbonyldiiron complex 2, which derived from N-(2-thienylmethylidene)aniline, undergoes (1) thermolysis to recover the original Schiff base 1, (2) reduction to form a hydrogenation product of the original thienyl Schiff base 3, (3) substitution to form a phosphine-substituted complex 4, and (4) chemical as well as electrochemical oxidation to produce a γ-lactam 5.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Synthesis ofN-aryl amines enabled by photocatalytic dehydrogenation

Catalytic dehydrogenation (CD)viavisible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access toN-aryl amines, which are widely utilized synthetic moieties,viavisible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis ofN-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactiveN-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.

Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines

Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.

HYDROGENATION OF IMINES WITH RU COMPLEXES

The present invention relates to the field of catalytic hydrogenation and to the use of ruthenium complexes in base-free hydrogenation processes for the reduction of imines into the corresponding amines.

Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ

A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.

Base-Mediated Amination of Alcohols Using Amidines

Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.

Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides

We present here an efficient method for the hydroboration of aldimines (-C=N-) with pinacolborane (HBpin) using an alkali metal catalyst, potassium benzyl. The reaction was accomplished with unprecedented catalytic efficiency under mild and solvent-free conditions to afford the high yield of the corresponding N-boryl amines up to 97percent. Various functionalities on aldimines were incorporated for hydroboration. The corresponding boryl amines were subjected to further hydrolysis to yield the corresponding secondary amines with good yields up to 89percent. This protocol for the reaction demonstrates an atom-economic and green method with diverse imines that bears excellent functional group tolerance. Chemoselective reduction of imines was also attained, with good yields of 74–89percent. We also propose the most plausible mechanism involving the formation of metal hydride as the active pre-catalyst.

Simple reversible fixation of a magnetic catalyst in a continuous flow system: Ultrafast reduction of nitroarenes and subsequent reductive amination using ammonia borane

Continuous reductive amination of aldehydes with nitroarenes over a Pd-Pt-Fe3O4 catalyst was performed. We used NH3BH3 as not only a hydrogen source for nitro reduction, but also a reductant for imine reduction. Secondary aromatic amines were obtained in the continuous flow reaction in good to excellent yields.

Band-Gap Narrowing of Highly Stable Heterogeneous ZrO2–ZnO Nanocomposites for the Reductive Amination of Carbonyl Compounds with Formic Acid and Triethylamine

The band gap of a material can be affected by factors such as size, doping materials, and oxygen vacancies. The decrease in band gap and change in state of ZrO2 with the addition of ZnO indicates interfacial interactions between ZrO2 and ZnO in the nanocomposites (NCs), which is further confirmed by the observed shift of the peaks in the Raman spectra. Heterobimetallic ZrO2–ZnO NCs were synthesized through a sustainable green approach by using sucrose isolated from Angelica gigas Nakai root extract. The highly stable NCs displayed excellent catalytic activity for reductive amination of carbonyl compounds utilizing HCO2H/(CH3CH2)3N as a hydrogen source. The high catalytic performance of the NCs was closely correlated with the narrow band gap and synergistic effect of ZrO2 with ZnO in the NCs.