435274-63-8

Upstream product

• 286-85-1 1H-cyclopropa[b]naphthalene 
• 62515-92-8 N-p-methoxyphenyl-2,4,6-cycloheptatriene-1-imine 
• 1379610-55-5 4,4,5,5-tetramethyl-2-(naphthalen-2-ylmethyl)-1,3,2-dioxaborolane 
• 104-94-9 4-methoxy-aniline 
• 1592-38-7 2-Naphthalenemethanol 
• 66-99-9 β-naphthaldehyde 
• 42101-92-8 2-naphthylmethyl methyl ether 
• 827-54-3 2-naphthylethylene 
• 3525-61-9 4-methoxy-N-(naphthalen-2-ylmethylene)aniline 

Downstream Products

• 1507344-48-0 C₁₉H₁₆N₂O 
• 3525-61-9 (E)-N-(4-methoxyphenyl)-1-(naphthalen-2-yl)methanimine 
• 1404296-21-4 2-((4-methoxyphenyl)amino)-2-(naphthalen-2-yl)acetonitrile 

Relevant academic research and scientific papers

[2 π + 2 σ] Type cycloaddition reactions of iminotropone derivatives with naphtho[b]cyclopropene to form cyclic amine compounds

Reactions of iminotropone derivatives with naphtho[b]cyclopropene under the presence of a catalytic amount of AgBF4 afforded cyclic amine derivatives via [2 π + 2 σ] type cycloaddition reactions. On the other hand, a reaction using a tropone hydrazone derivative without a catalysis formed a substituted hydrazone via a σ-bond rupture of the cyclopropene ring.

Chan-Lam Amination of Secondary and Tertiary Benzylic Boronic Esters

We report a Chan-Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines to form valuable alkyl amine products. Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition-metal-mediated transformation of a tertiary alkylboron reagent. Initial investigation into the reaction mechanism suggests that transmetalation from B to Cu occurs through a single-electron, rather than a two-electron process.

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.

Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations

Diethylsilane (Et2SiH2), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol-%) supported on TiO2. It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N-arylisoindolines is also shown in the reductive amination between o-phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N,2-diphenylisoindolin-1-imines are reduced stepwise to the isoindolines. Finally, Et2SiH2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au(0)-catalyzed protocols.

Nickel-Catalyzed Amination of α-Aryl Methyl Ethers

α-Aryl amines are prevalent in pharmaceutically active compounds and natural products. Herein, we describe a Ni-catalyzed protocol for their synthesis from readily available α-aryl ethers. While α-aryl ethers have been used as electrophiles in Ni-catalyzed C-C bond formations, their use in C-heteroatom bond formation is much less prevalent. Preliminary mechanistic insight suggests that oxidative addition is facilitated by an anionic ligand and that reductive elimination is a reversible process.

Ruthenium(II) complexes of pyridine-carboxamide ligands bearing appended benzothiazole/benzimidazole rings: Structural diversity and catalysis

A series of ruthenium(II) complexes (1–6) of pyridine-carboxamide ligands, HLBT/BI (HLBT = N-(benzo[d]thiazol-2-yl)picolinamide and HLBI = N-(1H-benzo[d]imidazol-2-yl)picolinamide), have been synthesized. All Ru(II) complexes have been characterized by using various spectroscopic techniques (FTIR, UV–Visible, 1H, 13C, 31P NMR and ESI-MS), conductivity and elemental analyses. The solid-state structures of all Ru(II) complexes, except 2, were substantiated by the single crystal X-ray diffraction technique that revealed versatile coordination modes of two bidentate ligands varying between N–N and N–O modes. All Ru(II) complexes exhibited a distorted octahedral geometry with a bidentate ligand while other coordination sites are occupied by either anionic Cl? or neutral co-ligands (CO, PPh3, CH3CN or (CH3)2SO). These well-defined ruthenium(II) complexes have been utilized as the homogeneous catalysts for the alkylation of amines using alcohols ensuing hydrogen borrowing strategy. Out of six complexes, 1 and 2 were found highly effective catalysts towards the N-alkylation of different amines with assorted alcohols. The alkylated products were obtained in excellent yields with good tolerance to a large variety of functional groups. To evaluate the role of putative Ru-hydride species as the intermediate during the catalytic cycle, the respective Ru-H complexes (7 and 8) were synthesized by the reaction of complexes 1 and 2 with NaBH4. Both Ru-H complexes were characterized using different spectroscopic techniques and crystallography. Importantly, both Ru-H complexes, 7 and 8, were directly able to alkylate imine using alcohol thus confirming the involvement of Ru-hydride species as the intermediates during the proposed catalytic cycle.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Synthesis of Chiral Cleft C,N-Palladium and Iridium Complexes from 2,3:6,7-Dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione and Their Synthetic Applications

A transition-metal-mediated functionalization of 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione is reported. By the use of the corresponding imine, iridium or palladium complexes were prepared, and they were well characterized by NMR and single-cry

Mononuclear half-sandwich iridium and rhodium complexes through C?H activation: Synthesis, characterization and catalytic activity

A series of mononuclear half-sandwich cyclometalated group 9 (Ir and Rh) metal complexes were synthesized in good yields through metal-mediated C?H bond activation. These air-stable C, N-chelate mode complexes have similar solid state structures. Both experimental results and DFT calculations confirmed that no binuclear complexes were generated in this reaction. The iridium complex 3a exhibited good catalytic activity for the reduction of both electron-rich and electron-poor aryl imines with low catalyst loading in the presence of formic acid/triethylamine (F/T) azeotropic mixture. All complexes were fully characterized by elemental analysis and IR and NMR spectroscopies. The structures of 1a, 1b, 2a, 3a and 4b (see chemical structure formula in Scheme 1 and Scheme 2) were further confirmed by single-crystal X-ray analysis.

Ruthenium-catalyzed reductive amination without an external hydrogen source

A ruthenium-catalyzed reductive amination without an external hydrogen source has been developed using carbon monoxide as the reductant and ruthenium(III) chloride (0.008-2 mol %) as the catalyst. The method was applied to the synthesis of antianxiety agent ladasten.