72931-45-4

Upstream product

• 75-21-8 oxirane 
• 119-64-2 tetralin 
• 100-42-5 styrene 
• 74-85-1 ethene 
• 693-03-8 n-butyl magnesium bromide 
• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 580-13-2 2-bromonaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 56-23-5 tetrachloromethane 
• 941-98-0 1'-naphthacetophenone 
• 1125-78-6 5,6,7,8-Tetrahydro-2-naphthol 
• 128-08-5 N-Bromosuccinimide 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 191-28-6 perixanthenoxanthene 
• 4832-38-6 naphthalene; compound with 1,3-dinitro-benzene 
• 624724-80-7 N-(naphthalen-1-yl)-1-phenylmethanesulfonamide 
• 24818-41-5 3-(naphthalen-1-yl)-3-phenylisobenzofuran-1(3H)-one 
• 854648-79-6 2,2-dimethyl-4-(naphthalen-2-yl)-4-oxobutanoic acid 
• 854904-16-8 2,2-dimethyl-4-[1]naphthyl-4-oxo-butyric acid 
• 860539-07-7 1-(naphthalen-1-yl)-2,2-diphenylethan-1-one 
• 95171-15-6 1-[2]naphthyl-dodecan-1-one 
• 116152-44-4 1,3,9-triphenyl-phenanthrene 
• 21416-60-4 naphthalene; compound with 2-chloro-1,3,5-trinitro-benzene 
• 19182-11-7 1,2-Diaethyl-naphthalin 
• 10275-58-8 2,7-di-tert-butylnaphthalene 
• 107100-92-5 (3-iodo-phenyl)-[1]naphthyl ketone 
• 6974-51-2 2-(naphthalen-1-yl)-2-phenylacetonitrile 

Relevant academic research and scientific papers

Synthesis, single crystal structures and efficient catalysis for tetralin oxidation of two novel complexes of Cu(II) with 2-aminomethyl pyridine

Two novel Cu(II) complexes were synthesized through the reaction of 2-aminomethyl pyridine (AMP) with CuCl2·2H2O by changing the metal/ligand ratio. Their structures were thoroughly characterized by FT-IR, elemental analysis and X-ray diffraction method. The results revealed that complex 1 [Cu(AMP)Cl2] consists of isolated binuclear molecules unit and displays distorted tetragonal pyramid. Complex 2 [Cu(AMP) 2(H2O)2]Cl2 exhibits a octahedral geometry. The complexes were both evaluated as catalysts in the tetralin oxidation with TBHP as oxidant. Complex 1 showed high catalytic activity and selectivity towards α-tetralone under mild conditions. Thus, under the optimized conditions (acetonitrile 10 ml, catalyst 0.045 mmol, tetralin 4.5 mmol, 65% TBHP 22.5 mmol, T = 50 °C), the conversion of tetralin reached 89% with a selectivity of 71% towards α-tetralone. Compared with complex 1, complex 2 displayed low catalytic activity mainly due to the strong steric hindrance from the two coordinated 2-aminomethyl pyridine molecules.

From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy

A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters can act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1°, 2°, 3°-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3°-3°, 3°-2°, and aryl-3° ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined experimental and computational studies identified a Ni0/NiI/NiIII pathway for ketone formation.

Efficient base-free hydrodehalogenation of organic halides catalyzed by a well-defined diphosphine-ruthenium(II) complex

A base-free, robust catalytic system based on the diphosphine-ruthenium(II) complex cation has been developed for the hydrodehalogenation of a wide range of aryl- and alkyl-chlorides/bromides (27 examples) with molecule hydrogen. Notably, the reaction proceeds at 120 °C with low catalyst loading (0.1 mol%) and exhibits a good tolerance toward functional groups, such as amido, carboxyl, sulfonyl, methoxyl, ester groups. All dehalogenation products are confirmed by GC, GC–MS and NMR spectroscopy. Moreover, a mechanism for the diphosphine-ruthenium(II) complex cation catalyzed dehalogenation process has been proposed. This hydrodehalogenation methodology shows a potential application for the organic transformation and degradation of organic halides.

Nickel-Catalyzed Photodehalogenation of Aryl Bromides

Herein, we describe a Ni-catalyzed photodehalogenation of aryl bromides under visible-light irradiation that utilizes tetrahydrofuran as hydrogen source. The protocol obviates the need for exogeneous amine reductants or photocatalysts and is characterized by its simplicity and broad scope, including challenging substrate combinations.

Cross-Coupling Reactions of Aryl Halides with Primary and Secondary Aliphatic Alcohols Catalyzed by an O,N,N-Coordinated Nickel Complex

A synthesis of alkyl aryl ethers was achieved via the cross-coupling of aryl halides with primary and secondary aliphatic alcohols catalyzed by a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. This nickel-catalyzed reaction proceeds smoothly in the absence of a phosphine ligand, affording alkyl aryl ethers in moderate to good yields. (Figure presented.).

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

Reduced Phenalenyl in Catalytic Dehalogenative Deuteration and Hydrodehalogenation of Aryl Halides

Dehalogenative deuteration reactions are generally performed through metal-mediated processes. This report demonstrates a mild protocol for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides (39 examples) using a reduced odd alternant hydrocarbon phenalenyl under transition metal-free conditions and has been employed successfully for the incorporation of deuterium in various biologically active compounds. The combined approach of experimental and theoretical studies revealed a single electron transfer-based mechanism.

A New Protocol for Catalytic Reduction of Alkyl Chlorides Using an Iridium/Bis(benzimidazol-2′-yl)pyridine Catalyst and Triethylsilane

The reduction of alkyl chlorides using triethylsilane is investigated. Primary, secondary, tertiary, and benzylic C-Cl bonds are effectively converted into C-H bonds using an [IrCl(cod)] 2/2,6-bis(benzimidazol-2′-yl)pyridine catalyst system. This catalyst system is quite simple since the tridentate N-ligand can be easily prepared in one step from commercially available reagents.

Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids

A suitable protocol for the photocatalytic decarboxylation of carboxylic acids was developed with metal-free ceramic boron carbon nitrides (BCN). With visible light irradiation, BCN oxidize carboxylic acids to give carbon-centered radicals, which were trapped by hydrogen atom donors or employed in the construction of the carbon-carbon bond. In this system, both (hetero)aromatic and aliphatic acids proceed the decarboxylation smoothly, and C-H, C-D, and C-C bonds are formed in moderate to high yields (35 examples, yield up to 93%). Control experiments support a radical process, and isotopic experiments show that methanol is employed as the hydrogen atom donor. Recycle tests and gram-scale reaction elucidate the practicability of the heterogeneous ceramic BCN photoredox system. It provides an alternative to homogeneous catalysts in the valuable carbon radical intermediates formation. Moreover, the metal-free system is also applicable to late-stage functionalization of anti-inflammatory drugs, such as naproxen and ibuprofen, which enrich the chemical toolbox.

Exploiting a silver-bismuth hybrid material as heterogeneous noble metal catalyst for decarboxylations and decarboxylative deuterations of carboxylic acids under batch and continuous flow conditions

Herein, we report novel catalytic methodologies for protodecarboxylations and decarboxylative deuterations of carboxylic acids utilizing a silver-containing hybrid material as a heterogeneous noble metal catalyst. After an initial batch method development, a chemically intensified continuous flow process was established in a simple packed-bed system which enabled gram-scale protodecarboxlyations without detectable structural degradation of the catalyst. The scope and applicability of the batch and flow processes were demonstrated through decarboxylations of a diverse set of aromatic carboxylic acids. Catalytic decarboxylative deuterations were achieved on the basis of the reaction conditions developed for the protodecarboxylations using D2O as a readily available deuterium source.