848-83-9

Usage

Chemical structure

A polycyclic aromatic hydrocarbon with a naphthalene core and two phenyl rings attached at the 1 and 3 positions.

Synthetic intermediate

Used in the production of pharmaceuticals, dyes, and other organic compounds.

Fluorescent probe

Utilized in biological and environmental research due to its strong fluorescence.

Stability

High stability, making it a valuable building block in organic synthesis and research applications.

Reactivity

Low reactivity, contributing to its stability and usefulness in various applications.

Handling

Should be handled with care due to potential health and environmental hazards if not properly managed.

Upstream product

• 1251-32-7 4-benzyl-2-tert-butyl-4,6-diphenyl-4H-pyran 
• 1177-68-0 4-benzyl-2,4,6-triphenyl-4H-thiopyran 
• 2589-31-3 N-benzylpyridinium bromide 
• 94-41-7 benzalacetophenone 
• 796-30-5 1,4-diphenylnaphthalene 
• 451-40-1 phenyl benzyl ketone 
• 536-74-3 phenylacetylene 
• 143192-60-3 2-(phenylethynyl)phenylacetylene 
• 71-43-2 benzene 
• 1064664-70-5 C₂₉H₂₄ 
• 1279102-54-3 (2-methylcyclohexa-1,3-dien-1-yl)(phenyl)methanone 
• 1279102-64-5 (Z)-trimethyl((2-methylenecyclohex-3-en-1-ylidene)(phenyl)methoxy)silane 
• 38986-89-9 trans-cinnamoyl fluoride 
• 1279102-74-7 2,4-diphenyl-1,2,5,6-tetrahydronaphthalene 

Downstream Products

• 809274-71-3 1-iodo-2,4-diphenylnaphthalene 

Relevant academic research and scientific papers

Experiment and Theory of Bimetallic Pd-Catalyzed α-Arylation and Annulation for Naphthalene Synthesis

We report the synthesis of bimetallic Pd(I) and Pd(II) complexes with bidentate 2-phosphinoimidazole ligands and their catalytic activity to generate substituted naphthalenes. This process involves the coupling of an aryl iodide and 2 equiv of a ketone via sequential ketone α-arylation and then annulation to generate disubstituted and tetrasubstituted naphthalenes in a regioselective manner. Excellent substrate scope for both aryl iodide and ketone partners is demonstrated, including that for heteroaryl iodides. Bimetallic Pd complexes are much more reactive than monometallic Pd catalysts in this transformation. Density functional theory calculations, isotope effect experiments, and substrate competition experiments were used to examine bimetallic mechanisms, reactivity, and selectivity.

Ruthenium-catalyzed coupling of α-carbonyl phosphoniums with sulfoxonium ylidesviaC-H activation/Wittig reaction sequences

A Ru(ii)-catalyzed coupling of various α-carbonyl phosphoniums with sulfoxonium ylides has been realized for the facile synthesis of 1-naphthols in good to excellent yields. This oxidant-free transformation proceeds through Ru-catalyzed C-H activation of phosphoniums, Ru-carbene insertion, and intramolecular Wittig reaction processes.

Ligand-Free and Solvent-Free Synthesis of 1,3-Disubstituted Naphthalenes through Stille Coupling

A variety of 1,3-disubstituted naphthalenes have been prepared by palladium-catalyzed annulation of (o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stille coupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C-C bond coupling.

Group 4 Diarylmetallocenes as Bespoke Aryne Precursors for Titanium-Catalyzed [2 + 2 + 2] Cycloaddition of Arynes and Alkynes

Despite the ubiquity of reports describing titanium (Ti)-catalyzed [2 + 2 + 2] cyclotrimerization of alkynes, the incorporation of arynes into this potent manifold has never been reported. The in situ generation of arynes often requires fluoride, which instead will react with the highly fluorophilic Ti center, suppressing productive catalysis. Herein, we describe the use of group 4 diarylmetallocenes, CpR2MAr2 (CpR = C5H5, C5Me5; M = Ti, Zr), as aryne precursors for the Ti-catalyzed synthesis of substituted naphthalenes via coupling with 2 equiv of an alkyne. Fair-to-good yields of the desired naphthalene products could be obtained with 1% catalyst loadings, which is roughly an order of magnitude lower than similar reactions catalyzed by palladium or nickel. Additionally, naphthalenes find broad applications in the electronics, photovoltaics, and pharmaceutical industries, urging the discovery of more economic syntheses. These results indicate that aryne transfer from a CpR2M(?2-aryne) complex to another metal is a viable route for the introduction of aryne fragments into organometallic catalytic processes.

Synthesis of Naphthalenyl Triflates via the Cationic Annulation of Benzodiynes with Triflic Acid

A highly efficient and regioselective annulation of benzodiynes promoted by triflic acid has been developed. This protocol provides a step and atom-economic access to a series of naphthalenyl triflates. Furthermore, direct synthetic applications of this r

Substituent-Guided Palladium-Ene Reaction for the Synthesis of Carbazoles and Cyclopenta[ b]indoles

An efficient palladium-catalyzed intramolecular Trost-Oppolzer type Alder-ene strategy was developed for the synthesis of carbazoles and cyclopenta[b]indoles from easily accessible(3-allyl-1H-indol-2-yl)methyl acetates. This strategy was extended for the synthesis of naphthalenes and dibenzobenzofurans as well. In addition, a short synthesis of antibacterial and antifungal natural product glycozoline and its analogues was also achieved.

Substituent-Guided Palladium-Ene Reaction for the Synthesis of Carbazoles and Cyclopenta[b]indoles

An efficient palladium-catalyzed intramolecular Trost-Oppolzer type Alder-ene strategy was developed for the synthesis of carbazoles and cyclopenta[b]indoles from easily accessible(3-allyl-1H-indol-2-yl)methyl acetates. This strategy was extended for the synthesis of naphthalenes and dibenzobenzofurans as well. In addition, a short synthesis of antibacterial and antifungal natural product glycozoline and its analogues was also achieved.

Palladium-Catalyzed Cascade Reaction of o-Bromobenzaldehydes with N-Sulfonylhydrazones: An Efficient Approach to the Naphthalene Skeleton

A new strategy for the construction of the naphthalene backbone is described. The reaction essentially starts from two simple aldehydes. The key step is enabled by a palladium-carbene migratory insertion. After that, a sequence of reversible allylic alkylation and intramolecular condensation takes place to give the substituted naphthalene derivatives. Additional manipulations on the sulfonyl group in the product via palladium-catalyzed Kumada coupling were also investigated. (Figure presented.).

Radical Addition/Cyclization Reaction of 2-Vinylanilines with Alkynes: Synthesis of Naphthalenes via Electron Catalysis

A cascade radical addition/cyclization reaction of 2-vinylanilines with alkynes for the synthesis of biologically important naphthalene derivatives is reported. In this transformation, the in-situ-formed diazonium salts from 2-vinylanilines served as efficient aryl radical precursors and the reaction was run under metal-free conditions.

Synthesis of Polysubstituted Polycyclic Aromatic Hydrocarbons by Gold-Catalyzed Cyclization-Oxidation of Alkylidenecyclopropane-Containing 1,5-Enynes

A gold-catalyzed tandem cyclization-oxidation of alkylidenecyclopropane-containing 1,5-enynes with 3,5-dibromo-pyridine N-oxide via a noncarbene model was developed, providing a range of synthetically valuable and useful arylacetaldehyde derivatives in mo