50844-92-3

Upstream product

• 578-51-8 2-bromobenzylchloride 
• 62-53-3 aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 32347-03-8 N-(2-bromobenzylidene)aniline 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 

Downstream Products

• 1234560-10-1 C₁₈H₂₀BrNO₂ 
• 1234559-97-7 C₂₁H₁₆BrNO₃ 
• 1234560-06-5 C₁₇H₁₆BrNO₃ 
• 1364806-34-7 3-imino-2-phenyl-2,3-dihydroisoquinoline-4-carbonitrile 
• 1393689-01-4 tert-butyl 2-(2-phenylisoindolin-1-yl)acetate 
• 573945-67-2 2-(2-bromophenyl)-2-(phenylamino)acetonitrile 
• 3340-78-1 2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 229-87-8 phenanthridine 
• 50844-93-4 5,6,5',6'-tetrahydro-[6,6']biphenanthridinyl 
• 5388-42-1 N-phenylphthalimidine 

Relevant academic research and scientific papers

Direct reductive amination of aromatic aldehydes catalyzed by gold(i) complex under transfer hydrogenation conditions

The direct reductive amination of aromatic aldehydes has been achieved with excellent isolated yields (89-96%) using readily accessible Ph 3PAuCl/AgOTf catalyst along with ethyl Hantzsch ester as hydrogen source under mild reaction conditions.

Molecular Oxygen-Mediated Radical Alkylation of C(sp3)-H Bonds with Boronic Acids

A direct and site-specific alkylation of (sp3)C-H bond with aliphatic boronic acid was achieved. By simply heating glycinates and amines together with alkylboronic acids under an oxygen atmosphere, a variety of unnatural α-amino acids and peptides could b

A Short Approach to N -Aryl-1,2,3,4-tetrahydroisoquinolines from N -(2-Bromobenzyl)anilines via a Reductive Amination/Palladium-Catalyzed Ethoxyvinylation/Reductive N -Alkylation Sequence

N -Aryl-1,2,3,4-tetrahydroisoquinolines are obtained via a convenient and short protocol with a broad range of substituents on both aromatic rings and high functional group tolerance. Starting from readily available ortho -brominated aromatic aldehydes and primary aromatic amines, condensation of these building blocks under reductive conditions gives N -aryl 2-bromobenzylamines. The C-3/C-4-unit of the tetrahydroisoquinoline is introduced using commercially available 2-ethoxyvinyl pinacolboronate under Suzuki conditions. Finally, the obtained crude ortho -ethoxyvinyl benzylamines are cyclized via an intramolecular reductive amination using the combination of triethylsilane/TFA to give the desired N -aryl-1,2,3,4-tetrahydroisoquinolines.

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.

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%.

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.

Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone

The cross-dehydrogenative coupling strategy for metal-free phosphonation and cyanation of secondary N-alkyl anilines has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to imine formation, then to respective α-aminophosphonates and α-aminonitriles was proposed.

Reactivity of Alkyne Insertion and Catalytic Activity of Five- and Six-Membered Cyclometalated Phosphine Complexes of Iridium

Reactions of three aryl-substituted phosphines with [Cp*IrCl2]2 afforded the corresponding five-membered or six-membered cyclometalated iridium complexes (2 or 5,6) via an intramolecular C(sp2)–H bond activation. Insertion reactions of the five-membered cycloiridated complex 2 with PhC≡CPh and PhC≡CCOPh resulted in the corresponding five-membered and six-membered doubly cycloiridated complexes 7 and 8, the formation of which presumably went through the vinylidene rearrangement of alkynes followed by 1,1-insertion; while the reactions of the six-membered cyclometalated complexes 5, 6 with PhC≡CPh or PhC≡CCOPh gave the corresponding eight-membered cycloiridated complexes 9–12 by 1,2-insertion. The hydrosilylation of imines catalyzed by five- or six-membered P-containing cycloiridated complexes were studied, and the results proved that the six-membered cycloiridated complex 5 can be used as an efficient catalyst, which was applied for the hydrosilylation of various imines, especially aldimines. Molecular structures of complexes 9, 10 and 12 were determined by X-ray diffraction.

Direct Reductive Amination of Aldehydes via Environmentally Benign Bentonite-Gold Nanohybrid Catalysis

An efficient, green and reliable method for the direct reductive amination of aldehydes was developed using an environmentally benign bentonite-gold nanohybrid catalyst. Use of this heterogeneous catalyst affords a variety of secondary amines in excellent yield under ambient reaction conditions in the presence of phenyldimethylsilane as mild hydride donor. The catalyst is recyclable, selective and is well applicable for the gram-scale preparation of secondary amines. (Figure presented.).

Magnetic nanoparticle-supported phosphine gold(i) complex: A highly efficient and recyclable catalyst for the direct reductive amination of aldehydes and ketones

The direct reductive amination of aldehydes and ketones has been achieved in dichloromethane at room temperature by using a magnetic nanoparticle-supported phosphine gold(i) complex [Fe3O4@SiO2-P-AuCl] as the catalyst and ethyl Hantzsch ester as the hydrogen source, yielding a variety of secondary amines in excellent yields under neutral conditions. The new heterogeneous gold catalyst can be prepared by a simple procedure from commercially readily available reagents and can easily be separated from the reaction mixture by applying an external magnet and recycled at least 10 times without any loss of activity.