471845-19-9

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 100-46-9 benzylamine 
• 446-51-5 2-fluorobenzyl alcohol 
• 69875-87-2 N-benzyl-1-(2-fluorophenyl)methanamine 
• 345-35-7 2-fluorobenzyl chloride 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 1072488-34-6 C₁₆H₁₆FN 
• 69875-87-2 N-benzyl-1-(2-fluorophenyl)methanamine 
• 1204705-04-3 (S)-2-(benzylamino)-2-(2-fluorophenyl)acetonitrile 
• 16064-04-3 2-(4-methoxyphenyl)benzaldehyde 
• 32832-95-4 2-benzylbenzaldehyde 

Relevant academic research and scientific papers

Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers

The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100percent, and various functionalized starting materials were accepted in an undivided electrochemical cell design. Moreover, a sensitivity assessment to ensure an improved reproducibility of the reaction and cyclic voltammetry experiments were performed to postulate a plausible reaction mechanism on their basis.

Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines

The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.

α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

Selective aerobic oxidation of halides and amines with an inorganic-ligand supported zinc catalyst

A practical, efficient and environmentally benign catalytic protocol for the oxidative cross-coupling reaction of halides with amines, oxidative self-coupling of amines and oxidation of halides was developed with inorganic-ligand supported ZnPOM (NH4)4[ZnMo6O18(OH)6] using molecular oxygen. This method mainly utilizes an inorganic polymolybdate ligand to support the Zn2+ ion, avoiding the use of complicated organic ligands.

Visible-Light-Driven Photocatalytic Oxidation of Organic Chlorides Using Air and an Inorganic-Ligand Supported Nickel-Catalyst Without Photosensitizers

Engineering photoredox-triggered chemical transformation via visible light has been an emerging area in organic synthesis. However, most of the well-established photocatalysts are based upon either transition metal complexes involved with noble metals and organic ligands or photosensitive organic dyes, the development of pure inorganic molecular photocatalysts that could provide better stability and durability is greatly retarded. Herein we discover that the Anderson polyoxometalate (POM) Na4[NiMo6O18(OH)6] (1), which consists of pure inorganic framework built from a central NiII core supported by six MoVIO6 inorganic scaffold/ligands, can be used as a powerful photocatalyst. Upon irradiation with visible light (>400 nm), the compound can catalyze, in high efficiency, a wide range of reactions, including the oxidative cross-coupling reaction of chlorides with amines, as well as oxidation of chlorides using molecular oxygen, affording various imines, aldehydes, and ketones, respectively in high selectivity and good yields. Owing to the robust inorganic framework, this catalyst exhibits excellent stability during the catalysis and reusability with little loss of the catalytic activity, thus providing an alternative without use of complicated organic ligands and expensive noble metal-based photosensitizers.

Transition-Metal-Controlled Inorganic Ligand-Supported Non-Precious Metal Catalysts for the Aerobic Oxidation of Amines to Imines

Most state-of-art transition-metal catalysts usually require organic ligands, which are essential for controlling the reactivity and selectivity of reactions catalyzed by transition metals. However, organic ligands often suffer from severe problems including cost, toxicity, air/moisture sensitivity, and being commercially unavailable. Herein, we show a simple, mild, and efficient aerobic oxidation procedure of amines using inorganic ligand-supported non-precious metal catalysts 1, (NH4)n[MMo6O18(OH)6] (M=Cu2+; Fe3+; Co3+; Ni2+; Zn2+, n=3 or 4), synthesized by a simple one-step method in water at 100 °C, demonstrating that the catalytic activity and selectivity can be significantly improved by changing the central metal atom. In the presence of these catalysts, the catalytic oxidation of primary and secondary amines, as well as the coupling of alcohols and amines, can smoothly proceed to afford various imines with O2 (1 atm) as the sole oxidant. In particular, the catalysts 1 have transition-metal ion core, and the planar arrangement of the six MoVI centers at their highest oxidation states around the central heterometal can greatly enhance the Lewis acidity of catalytically active sites, and also enable the electrons in the center to delocalize onto the six edge-sharing MO6 units, in the same way as ligands in traditional organometallic complexes. The versatility of this methodology maybe opens a path to catalytic oxidation through inorganic ligand-coordinated metal catalysis.

Factors influencing the regioselectivity of the oxidation of asymmetric secondary amines with singlet oxygen

Aerobic amine oxidation is an attractive and elegant process for the α functionalization of amines. However, there are still several mechanistic uncertainties, particularly the factors governing the regioselectivity of the oxidation of asymmetric secondary amines and the oxidation rates of mixed primary amines. Herein, it is reported that singlet-oxygen-mediated oxidation of 1° and 2° amines is sensitive to the strength of the α-C-H bond and steric factors. Estimation of the relative bond dissociation energy by natural bond order analysis or by means of one-bond C-H coupling constants allowed the regioselectivity of secondary amine oxidations to be explained and predicted. In addition, the findings were utilized to synthesize highly regioselective substrates and perform selective amine cross-couplings to produce imines.

Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

(Figure presented) A highly active and enantioselective titanium-catalyzed cyanatlon of imines at room temperature Is described. The catalyst used Is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields In 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.

Carbonic anhydrase-encoded dynamic constitutional libraries: Toward the discovery of isozyme-specific inhibitors

A constitutional dynamic library (CDL) was generated under thermodynamic control by using the amino-carbonyl/imine interconversion as reversible chemistry, combined with noncovalent bonding within the active site of the metalloenzyme carbonic anhydrase (C

Synthesis of novel 2-alkoxy-3-amino-3-arylpropan-1-ols and 5-alkoxy-4-aryl-1,3-oxazinanes with antimalarial activity

A variety of novel syn-2-alkoxy-3-amino-3-arylpropan-1-ols was prepared through LiAlH4-promoted reductive ring-opening of cis-3-alkoxy-4-aryl-β-lactams in Et2O. The latter γ-aminoalcohols were easily converted into cis-5-alkoxy-4-aryl-1,3- oxazinanes using formaldehyde in THF. Both series of compounds were evaluated against a chloroquine sensitive strain of Plasmodium falciparum (D10), revealing micromolar potency for almost all representatives. Eleven compounds exhibited antimalarial activity with IC50 values of ≤30 μM, and the majority of these compounds did not show cytotoxicity at the concentrations tested.