91000-43-0

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 100-51-6 benzyl alcohol 
• 124043-95-4 N-benzyl-3,5-dimethylaniline 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 99-12-7 5-nitro-m-xylene 

Downstream Products

• 1075-70-3 benzaldehyde N,N-dimethylhydrazone 
• 1448450-28-9 2-(3,5-dimethylphenyl)-3-phenylisoquinolin-1(2H)-one 
• 150004-24-3 N,N-dibenzyl-3,5-dimethylaniline 
• 124043-95-4 N-benzyl-3,5-dimethylaniline 
• 1453874-99-1 methyl 1-(3,5-dimethylphenyl)-4-(2-methoxy-2-oxoethyl)-5-phenyl-1H-pyrrole-3-carboxylate 
• 1438900-71-0 N⁴,N^4'-dibenzyl-2,2',6,6'-tetramethyl-[1,1'-biphenyl]-4,4'-diamine 

Relevant academic research and scientific papers

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys

Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex

Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading of base results in the amine product. This strategy on product selectivity also strongly depends on the organometallic catalysts in use. We expect that the present study could provide useful insights toward selective organic synthesis and catalyst design.

Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis

A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.

Ni-Catalyzed asymmetric reduction of α-keto-β-lactams: via DKR enabled by proton shuttling

Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone. This journal is

Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides

A transition metal-free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2-aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatible and green reaction conditions such as, solvent, room temperature reactions and transition metal-free approach. Moreover, it offers a broader substrate scope.

Substituent effects on the stretching vibration of C═N in multi-substituted benzylideneanilines

Forty-nine samples of 3,4′/4,3′/3,3′-disubstituted benzylideneanilines (XBAYs) and 52 samples of multi-substituted XBAYs were synthesized, and their infrared absorption spectra were recorded in this paper. On the basis of the stretching vibration frequencies νC═N of C═N bridging bond of 158 samples of substituted XBAYs (including 57 samples of 4,4′-disubstituted XBAYs from reference and 101 samples of substituted XBAYs synthesized in this paper), an extensional research of substituent effects on the νC═N values from 4,4′-disubstituted XBAYs to multi-substituted XBAYs was made. A modified equation for quantifying the νC═N values of multi-substituted XBAYs was obtained (shown as Equation (3)). Equation (3) indicates that the excited-state substituent constant of Y and the substituent specific cross-interaction effect between X and X cannot be ignored for the quantitative regression analysis of the νC═N values of multi-substituted XBAYs. Compared with Equation (1), Equation (3) has a wider application and more accuracy in quantifying the νC═N values of substituted XBAYs.

Central-to-Axial Chirality Conversion Approach Designed on Organocatalytic Enantioselective Povarov Cycloadditions: First Access to Configurationally Stable Indole–Quinoline Atropisomers

The first stereoselective synthesis of enantioenriched axially chiral indole–quinoline systems is presented. The strategy takes advantage of an organocatalytic enantioselective Povarov cycloaddition of 3-alkenylindoles and N-arylimines, followed by an oxi

Manganese-Catalyzed and Base-Switchable Synthesis of Amines or Imines via Borrowing Hydrogen or Dehydrogenative Condensation

The use of earth-abundant transition metals as a noble metal replacement in catalysis is especially interesting if different catalytic reactivity is observed. We report, here, on the selective manganese-catalyzed base-switchable synthesis of N-alkylated amines or imines. In both reactions, borrowing hydrogen/hydrogen autotransfer (N-alkyl amine formation) or dehydrogenative condensation (imine formation), we start from the same amines and alcohols and use the same Mn precatalyst. The key is the presence of a potassium base to prefer N-alkylation and a sodium base to permit imine formation. Both bases react with the manganese hydride via deprotonation. The potassium manganate hydride reacts about 40 times faster with an imine to give the corresponding amine than the sodium manganate hydride. The selectivity seems unique for manganese complexes. We observe a broad scope with a complete product overlap, all amine alcohol combinations can be converted into an N-alkyl amine or an imine, and a good functional group tolerance.

Interrupted imino-nazarov cyclization of 1-aminopentadienyl cation and related cascade process

Facile 4π conrotatory imino-Nazarov cyclization of a 1-aminopentadienyl cation generated from condensation an aldehyde and secondary aniline in the presence of a catalytic amount of a Lewis acid has been developed. Silver(I)-catalyzed intramolecular arene trapping of the resulting cyclic oxyallyl cation leads to formation of tricyclic indoline-fused cyclopentanone. The use of lanthanide salts allows transformation after the initial trapping to afford tetrahydroquinoline-fused cyclopentenone in a concise manner. Taking control: The fate of an oxyallyl cation formed through a 4π conrotatory imino-Nazarov cyclization can be controlled to access cyclopentanoid frameworks. In the presence of silver(I), intramolecular arene trapping leads to indoline-fused cyclopentanones. Gadolinium(III) facilitates a cascade transformation to furnish tetrahydroquinoline-fused cyclopentenones. Tf=trifluoromethanesulfonyl.

Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2, 3,4-tetrahydroquinolines via an AA′BC sequential four-component reaction and their application to 2-arylquinoline synthesis

The CAN-catalyzed reaction between 3,5-disubstituted anilines, vinyl ethers and aromatic aldehydes leads to trans-2-aryl-4-arylaminotetrahydroquinolines, in an AA′BC sequential multicomponent transformation related to the Povarov reaction that was also extended to the use of a second aniline as the C-4 substituent. The unusual trans stereochemistry was explained by stabilization of the corresponding intermediate by intramolecular hydrogen bonding. The presence of the 4-anilino substituent allowed adapting the method to the synthesis of 4-unsubstituted 2-arylquinolines, by treatment of the crude product from the MCR with FeCl3 in methanol.