15110-93-7

Upstream product

• 348-54-9 2-Fluoroaniline 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 

Downstream Products

• 288094-34-8 (R,R)-2,6-bis(2-isopropylphenyl)-3,5-dimethylphenyl 3-(2-fluorophenyl)amino-3-phenylpropionate 
• 1336913-34-8 2-fluoro-N-(4-phenoxy-1-phenylbut-2-yn-1-ylidene)benzenamine 
• 1204-43-9 2-(4-methylphenyl)aniline 
• 123330-52-9 N-benzyl-(2-fluorophenyl)amine 

Relevant academic research and scientific papers

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

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%.

Switching the N-Alkylation of Arylamines with Benzyl Alcohols to Imine Formation Enables the One-Pot Synthesis of Enantioenriched α-N-Alkylaminophosphonates

The selective N-alkylation of anilines with benzylic alcohols can be switched in favor of the dehydrogenative condensation process using the nitrile-ligated Kn?lker's complex by conducting the reaction either in a closed system under inert conditions, or in an open system in air. The selective formation of imines, containing reactive C=N bonds, provides an opportunity towards further functionalization. Indeed, a one-pot three-component condensation of alcohols, amines and phosphites, promoted by an iron-based Kn?lker-type complex in combination with a chiral BINOL-based phosphoric acid, provides access to enantioenriched α-N-alkylaminophosphonates.

C–H Bond Functionalization of 1,4-Benzoquinone by Silver-Mediated Regioselective Phosphination and Amination Reactions

The one-pot synthesis of 2,5-bis(diarylphosphoryl)-3,6-bis(arylamino)cyclohexa-2,5-diene-1,4-diones has been achieved by AgI-mediated full C–H functionalization of 1,4-benzoquinone (BQ) through regioselective dual phosphination and amination reactions. BQ, diarylphosphine oxides [SPOs, Ar2PH(=O)], and imines reacted to give the products under mild conditions. 1,4-Naphthoquinone (NQ) could also be used instead of BQ. When aniline was used instead of the corresponding imine, a lower yield of the desired product was obtained. In the absence of Ag2CO3, hydrophosphinylation of the imine by the SPO occurred as a competitive side-reaction. AgI plays versatile roles in this reaction, as a mediator for facilitating the consecutive additions of Ar2P(=O)– and aniline to the related β-carbon atoms of BQ, as an oxidant of hydroquinone (HQ) intermediates to form the substituted BQ counterpart, and as an inhibitor of the hydrophosphinylation side-reaction of the imine by the SPO. The X-ray crystal structures of several new products have been determined. A reaction mechanism is also proposed based on the experimental results.

Lanthanides Mediated Oxidative Cross Coupling of Benzylalcohol and Various Amines to Form Corresponding Imines

Herein, a new and efficient approach towards the oxidative cross-coupling of benzylalcohol and various aromatic amines to form corresponding imines with high degree conversion (>80 %) and chemo-selectivity using lanthanide salts as pre-catalysts is presented. The catalyzed oxidative cross-coupling reaction using La(NO3)3·6H2O as pre-catalyst displayed a broad substrate scope. The reaction afforded various substituted imines from the reaction of benzylalcohol with ample variety of amines in good yields.

NaOH-catalyzed imine synthesis: Aerobic oxidative coupling of alcohols and amines

The convenient transition-metal-free synthesis of imines through oxidative coupling of alcohols and amines is reported. The reaction is catalyzed by NaOH (10 mol-%) and is performed with air as an oxidant in the absence of any co-solvent. The convenient transition-metal-free synthesis of imines through oxidative coupling of alcohols and amines is reported. The reaction is catalyzed by NaOH (10 mol-%) and is performed with air as an oxidant in the absence of any co-solvent. Copyright

Structural investigation of weak intermolecular interactions in fluorine substituted isomeric N-benzylideneanilines

The study of the influence of aromatic C-F group in directing crystal packing is an important area of current research. The role of the aromatic C-F group in the formation of weak intermolecular interactions in the absence of strong hydrogen bond donors a

CuBr/FeCl3 catalysis: A novel and efficient method for the preparation of new aryl (Iminomethyl)propargyl ether derivatives via C-H activation of aryl propargyl ethers

CuBr/FeCl3 Catalysis as a novel and efficient method has been developed for the preparation of new aryl propargyl imine ether derivatives via C-H activation of aryl propargyl ethers, followed by reaction with imines generated from aldehydes and amines. Copyright

Nickel-catalyzed multi-component connection reaction of isoprene, aldimines (lactamines), and diphenylzinc

Ni(acac)2 catalyzes the four-component connection reaction of diphenylzinc, isoprene, aromatic aldehydes, and aromatic amines in this order and provides stereochemically homogeneous (E)-1-arylamino-1-aryl-3-methyl-5-phenyl-3-pentenes (1) in excellent yields. Aliphatic aldehydes react similarly and give (E)-1-arylamino-1-alkyl-3-methyl-5-phenyl-3-pentenes (1) in slightly reduced yields. When the alkyl groups are bulky, in addition to 1 are formed (E)-1-arylamino-1-alkyl-4-methyl-5-phenyl-3-pentenes (1′) as the minor products. Lactamines prepared in situ from five- and six-membered lactols and aromatic amines are more reactive than alkyl aldehyde aldimines and furnish (E)-4-arylamino-6-methyl-8-phenyl-6-octen-1-ols (4) and (E)-5-arylamino-7-methyl-9- phenyl-7-nonen-1-ols (5), respectively, in good yields with excellent E-stereoselectivity.

Hydrosilylation of (hetero)aromatic aldimines in the presence of a Pd(I) complex

The reaction of triethylsilane with heterocyclic and aromatic azomethines, catalyzed by the [Pd(allyl)Cl]2 complex, was studied. It was found that the reaction is affected by the nature of the functional groups in the aza and methine parts of the aldimine molecules, which were produced by the condensation of furan, thiophene, and benzene aldehydes with aniline and its derivatives. The reactivity of a series of imines is compared with their electronic and structural characteristics, determined by quantum-chemical methods. The corresponding furan, thiophene, and aromatic amines and also certain silylamines were synthesized.