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Upstream product

• 16587-59-0 3-phenylnaphtho[2,1-b]thiophene 
• 190189-36-7 1-naphthyl 2-phenylpropanoate 
• 941-98-0 1'-naphthacetophenone 
• 90-14-2 1-Iodonaphthalene 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 
• 102421-44-3 4-methyl-N'-(1-(naphthalen-1-yl)ethylidene)benzenesulfonohydrazide 
• 98-80-6 phenylboronic acid 
• 1127-76-0 1-ethylnapthelene 
• 585-71-7 (1-bromoethyl)benzne 
• 68716-52-9 1-naphthylboronic acid pinacol ester 
• 642-28-4 phenyl(1-naphthyl)methanol 
• 91-20-3 naphthalene 
• 98-85-1 1-Phenylethanol 
• 91-60-1 2-Naphthalenethiol 

Relevant academic research and scientific papers

A general copper-catalyzed radical C(sp3)?C(sp2) cross-coupling to access 1,1-diarylalkanes under ambient conditions

A general copper-catalyzed C(sp3)?C(sp2) cross-coupling of (hetero)benzyl bromides with the air- and moisture-stable aryl nucleophiles has been developed, providing a facile access to pharmaceutically useful 1,1-di(hetero)arylalkane and 1-aryl-1-heteroarylalkane scaffolds. Critical to the success is the utilization of a proline-based N,N,P-ligand to enhance the reducing capability of copper, thus easily converting benzyl bromides to the corresponding radical species via a single-electron transfer process under ambient conditions. The reaction features a broad substrate scope, covering (hetero)arylboronate esters, oxadiazoles, and benzo[d]oxazoles, as well as primary and secondary (hetero)benzyl bromides with excellent functional group tolerance.

Synthesis of 1,1′-diarylethanes and related systems by displacement of trichloroacetimidates with trimethylaluminum

Benzylic trichloroacetimidates are readily displaced by trimethylaluminum under Lewis acid promoted conditions to provide the corresponding methyl substitution product. This method is a convenient way to access 1,1′-diarylethanes and related systems, which play a significant role in medicinal chemistry, with a number of systems owing their biological activity to this functionality. Most benzylic substrates undergo ready displacement, with electron deficient systems being the exception. The use of an enantiopure imidate showed significant racemization, implicating the formation of a cationic intermediate.

One-pot reductive coupling reactions of acetyl naphthalene derivatives, tosylhydrazide, with arylboronic acids

In this study, a one-pot two-step reductive coupling between acetyl naphthalene derivatives, tosylhydrazide, and arylboronic acids, affording substituted 1(or 2)-(1-phenylethyl)naphthalenes in moderate-to-excellent yields, was reported. Notably, solvent played a crucial role in the coupling of 1-acetyl naphthalene derivatives (toluene) or 2-acetyl naphthalene derivatives (1,4-dioxane) as starting materials. Meanwhile, the scope of this one-pot coupling reaction was extended to 1(or 2)-naphthaldehyde substrates. Particularly, the system was also suitable to synthesize 1(or 2)-(1-phenylethyl)naphthalenes on a multi-gram scale, and was applied in the synthesis of naphthylmethyl substituted carbazolyl compounds.

Copper-Catalyzed Arylation of Benzylic C-H bonds with Alkylarenes as the Limiting Reagents

A novel copper-catalyzed arylation of benzylic C-H bonds with nucleophilic arylboronic acids has been developed that provides an efficient way to synthesize various 1,1-diarylalkanes with a broad substrate scope and excellent functional group compatibilit

Method for efficiently synthesizing 1,1-diaryl alkane compound

The invention discloses a method for efficiently synthesizing a 1,1-diaryl alkane compound. The method comprises the step of reacting by virtue of a compound of formula I (shown in the description) and a compound of a formula II (shown in the description) in the presence of a copper catalyst, a dinitrogen ligand, alkali and an oxidant under the protection of gas, so as to obtain a compound of formula III. The method has the advantages that reaction conditions are mild, the operation is simple, a substrate is wide in adaptability, functional groups are high in compatibility, and the like. The method has relatively high academic values and application values.

Highly chemoselective and enantiospecific Suzuki-Miyaura cross-couplings of benzylic organoboronic esters

The use of potassium carbonate in addition to silver oxide is shown to increase the enantiospecificity of the Suzuki-Miyaura cross-coupling reaction of chiral secondary benzylic boronic esters. From mechanistic studies, it is shown that the reaction is co

Tin exchanged heteropoly tungstate: An efficient catalyst for benzylation of arenes with benzyl alcohol

The partial exchange of tin with the protons of 12-tungstophosphoric acid (TPA) results in a highly active heterogeneous catalyst for benzylation of arenes with benzyl alcohol as benzylating agent. The catalysts were characterized by X-ray diffraction, Laser-Raman and FT-IR of pyridine adsorption. The catalytic activity depends significantly on the extent of tin exchanged with the protons of heteropoly tungstate. The characterization results suggest the presence of Lewis acidic sites by the exchange of tin. The catalyst with partial exchange of Sn showed high benzylation activity, which in turn related to variation in acidity of the catalysts. The catalyst is highly active for benzylation reaction irrespective of the nature of substituted arenes and benzyl alcohols. These catalysts are highly active compared to other acid catalysts used for benzylation of different arenes. The catalyst is easy to separate from reaction mixture and exhibit consistent activity upon reuse. The plausible reaction mechanism based on the role of both Lewis and Bronsted acid sites of the catalyst was discussed.

Enantiodifferentiation of a silane and the analogous hydrocarbon by the dirhodium method-silane...dirhodium complex interaction

Chiral silane 1 was enantiodifferentiated by recording NMR spectra in the presence of the chiral dirhodium complex Rh2(II) [(R) - (+) - MTPA4] (Rh*). This is the first report of direct chiral recognition by spec

Mediation of photochemical reactions of 1-naphthyl phenylacylates by polyolefin films. A 'radical clock' to measure rates of radical-pair cage recombinations in 'viscous space'

The fates of phenylacyl/1-naphthoxy singlet radical pairs generated upon irradiation of 1-naphthyl phenylacetate (1a) and 1-naphthyl 2-phenylpropanoate (1b) in three unstretched and stretched polyethylene films and isotactic and syndiotactic polypropylene films have been investigated. From dynamic fluorescence measurements the primary locus of reactions by 1 is within amorphous regions of the films. The reaction cages afforded by these media inhibit escape of the radical pairs and mediate their reorientational motions leading to photo-Fries and related products. In essence, the cages act as stiff-walled templates. In addition, a method is described to measure the rate constants for the singlet radical pairs. Thus, the rate constants (leading to the keto precursors) of the 2-phenylacyl-1-naphthols from the radical pairs of 1 (> 108 s-1) are >6 times the rate constants for the 4-isomers. Film stretching increases this selectivity but there is no obvious correlation between the rate of the in-cage radical pair recombinations and macroscopic polymer, properties such as degree of crystallinity and frequency of branched chains. By contrast, formation of (the keto precursors of) 2-benzylic-1-naphthols (from in-cage recombinations after phenylacyl decarbonylation) is slower than for the 4-benzyl-1-naphthols. (C) 2000 Elsevier Science Ltd.

Palladium-Catalyzed Methylation of Aryl and Vinyl Halides by Stabilized Methylaluminum and Methylgallium Complexes

The intramolecularly stabilized mono- and dialkylaluminum complexes 1a, 2, 3, 4a, 5a, 5c, 6a, 6c, 7, 8, and 9 in the presence of palladium catalysts, cross-alkylate aryl, vinyl, and benzyl bromides and iodides under mild standard laboratory conditions. Aryl bromides with carbonyl substituents or benzylic halides are converted partially into dialkyl compounds. Under similar conditions, the analogous stabilized dimethylgallium complexes 1b, 4b, 5b, 6b, and 10 methylate aryl and vinyl bromides and iodides in a highly selective manner. Substituted bromobenzenes XC6H4Br, where X = CHO, COPh, CO2Et, CN, NO2, Cl, CH2Br, or CH=CHCOPh, are methylated by the organogallium reagents usually only at the aromatic ring halogen atom to give substituted toluenes as single products. The methylation rates were shown to depend on the nature of the chelating ligands, on the solvent, and on the type of palladium catalyst employed.