169323-56-2

Upstream product

• 66-77-3 1-naphthaldehyde 
• 37782-11-9 benzylmagnesium iodidide 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 605-85-6 1-(1-naphthyl)-2-phenylethanone 
• 86-55-5 1-naphthalenecarboxylic acid 
• 2459-24-7 methyl 1-naphthoate 
• 90-14-2 1-Iodonaphthalene 
• 122-78-1 phenylacetaldehyde 
• 96-09-3 styrene oxide 
• 13922-41-3 1-Naphthylboronic acid 

Downstream Products

• 2840-87-1 (E)-1-styrylnaphthalene 
• 127529-47-9 1-(1-[1]naphthyl-2-phenyl-ethyl)-piperidine 
• 36707-32-1 1-(1-naphthyl)-2-phenylethane 
• 116218-05-4 1-(1’-chloro-2’-phenylethyl)naphthalene 

Relevant academic research and scientific papers

Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand

We report a catalytic method to access secondary alcohols by the coupling of aryl iodides. Either aldehydes or alcohols can be used as reaction partners, making the transformation reductive or redox-neutral, respectively. The reaction is mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2ligand, which has previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism is proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alcohol reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcohols, demonstrating control over the oxidation state of both the starting materials and products.

Pd-catalyzed allylative dearomatisation using Grignard reagents

Pd-catalyzed allylative dearomatisation of naphthyl halides is shown to be feasible by employing Grignard reagents. The high reactivity of the nucleophile allows for fast reactions and low catalyst loading, while a plethora of successfully substituted compounds illustrate the broad scope. Five membered heteroaromatic compounds are also demonstrated to be reactive under similar conditions.

Synthetic method for diaryl-substituted ethanol compound serving as medical intermediate

The invention relates to a synthetic method for a diaryl-substituted ethanol compound serving as a medical intermediate shown as a formula (III). The method comprises the following steps: reacting a compound shown as a formula (I) and a compound shown as a formula (II) in a hermetic way in an organic solvent in the presence of a catalyst and an alkali; performing posttreatment at the end of the reaction to obtain a compound shown as the formula (III), wherein R1 and R2 are independently selected from H, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms or halogen; or R2 and a benzene ring which is connected with the R2 form a naphthalene ring. According to the synthetic method, the diaryl-substituted ethanol compound can be obtained at a high yield through comprehensive selection and coordination of a specific reaction substrate, the catalyst, the alkali and the organic solvent, and has good application prospect and industrial production potential in the field of synthesis of medical intermediates.

Asymmetric transfer hydrogenation of 1-naphthyl ketones by an ansa-Ru(II) complex of a DPEN-SO2N(Me)-(CH2)2(η 6-p-tol) combined ligand

The first second-generation designer Ru(II) catalyst 1b featuring an enantiopure N,C-(N-ethylene-N-methyl-sulfamoyl)-tethered (DPEN- κ2N,N′)/η6-toluene hybrid ligand is introduced. Using an S/C = 1000 in HCO2H-Et3N 5:2 transfer hydrogenation medium, secondary 1-naphthyl alcohols are obtained in up to >99.9% ee under mild conditions. Mechanistic factors are discussed.

Cadmium-mediated carbonyl benzylation in tap water

Zn/CdCl2 has been developed as a mediator in the benzylation of various aldehydes in tap water affording the corresponding alcohols in moderate to good yields. The addition of a catalytic amount of InCl3 increases the yield of benzylation product significantly. It can selectively mediate the benzylation of aldehydes in the presence of ketones. A mechanism involving the formation of a cation π-complex is proposed based on the experimental facts. Georg Thieme Verlag Stuttgart.

MODERN FRIEDEL-CRAFTS CHEMISTRY. XIX THE EFFECT OF REACTION VARIABLES ON PRODUCT DISTRIBUTIONS DURING SOME INTER- AND INTRAMOLECULAR ALKYLATION AND ACYLATIONS OF NAPHTHALENE

The effect of reaction variables (catalyst, solvebt, time and temperature) on the α, β-orientation during benzylation, benzoylation, β-phenylethylation and phenylacetylation of naphthalene as well as on inter- vs intramolecular reactions of 1-naphthylacetyl chloride and benzene were explored.The identities and quantities of the products were determined by glpc, IR, and NMR using authentically prepared reference samples.The results demonstrated that: (1) In almost all cases, both α- and β-isomers were produced but in different proportions. (2) Complexed AlCl3-CH3NO2 and AlCl3-PhNO2 catalysts favoured β- over α-orientation in reactions of naphthalene and inter- over intramolecular pathway in reactions of 1-naphthylacetyl chloride and benzene. (3) Evidences for reorientation in benzylation and benzoylation of naphthalene and for phenonium ion intermediacy in alkylation with β-phenylethyl bromide are presented.