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Usage

Uses

Used in Organic Synthesis:
1-(2-((4-fluorophenyl)ethynyl)phenyl)ethanone is used as a building block for the synthesis of various functional organic materials. Its unique structure allows for the creation of a wide range of compounds with different properties and applications.
Used in Pharmaceutical Research:
1-(2-((4-fluorophenyl)ethynyl)phenyl)ethanone is used as a compound in pharmaceutical research for its potential pharmacological properties. It is being investigated for its potential applications in drug development and medicinal chemistry, where its unique structure may contribute to the discovery of new therapeutic agents.
Used in Drug Development:
In the pharmaceutical industry, 1-(2-((4-fluorophenyl)ethynyl)phenyl)ethanone is used as a starting material for the development of new drugs. Its structural features make it a promising candidate for the design and synthesis of novel therapeutic compounds with potential applications in treating various diseases and medical conditions.

Upstream product

• 88-65-3 2-bromobenzoic-acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 2142-70-3 2-iodoacetophenone 
• 2142-69-0 2-bromophenyl methyl ketone 

Downstream Products

• 1606161-26-5 12-methyl-5-(4-fluorophenyl)-6-(4-fluorobenzoyl)chrysene 

Relevant academic research and scientific papers

Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives

An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.

Palladium-Catalyzed Dialkylation of C-C Triple Bonds: Access to Multi-Functionalized Indenes

A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.

CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones

A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.

Copper-Catalyzed Cascade Cyclization of Arylsulfonylhydrazones Derived from ortho-Alkynyl Arylketones: Regioselective Synthesis of Functionalized Cinnolines

A novel copper-catalyzed cascade reaction of arylsulfonylhydrazones derived from ortho-alkynyl arylketones was accomplished. This reaction provides concise access to diversified cinnolines in good yields. The mechanistic investigations have disclosed involvement of the key alkynyl amination, 1,4-aryl migration, desulfonylation, and diazo radical cyclization cascade in the transformation.

Radical-Triggered Tandem Cyclization of 1,6-Enynes with H2O: A Way to Access Strained 1 H-Cyclopropa[ b]naph thalene-2,7-diones

A radical-triggered tandem cyclization of 1,6-enynes has been developed herein. Strained 1H-cyclopropa[b]naphthalene-2,7-diones are successfully obtained in moderate to good yields with excellent stereoselectivity. Mechanistic studies reveal a key role of water in generating a hydroxyl radical that initiates a sequential Michael addition/ring closure pathway. Importantly, the formed hydroxyl is proposed to be a good leaving group during the cyclopropane ring formation.

Asymmetric Hydrogenation of In Situ Generated Isochromenylium Intermediates by Copper/Ruthenium Tandem Catalysis

The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting of Cu(OTf)2 and a chiral cationic ruthenium–diamine complex. A range of chiral 1H-isochromenes were obtained in high yields with good to excellent enantioselectivity. These chiral 1H-isochromenes could be easily transformed into isochromanes, which represent an important structural motif in natural products and biologically active compounds. The chiral induction was rationalized by density functional theory calculations.

Selective construction of polycyclic spirooxindoles: Via a Cu(OTf)2/HOTf-catalyzed domino reaction of o -arylalkynylacetophenones and 3-phenacylideneoxindoles

Under the combined catalysis of Cu(OTf)2/HOTf, the domino annulation reaction of o-arylalkynyl acetophenones with 3-phenacylideneoxindoles in refluxing acetonitrile selectively afforded functionalized spiro[indoline-3,7′-tetrapheno[7,6-bc]furan

Catalytic Sulfur-Enabled Dehydrobicyclization of 1,6-Enynes toward Arylated Indeno[1,2-c]thiophenes

A new copper-catalyzed sulfur-enabled dehydrobicyclization of 1,6-enynes using potassium sulfide as a sulfurating reagent has been established, providing a straightforward access toward arylated indeno[1,2-c]thiophenes with moderate to good yields. This sulfur incorporation pathway involves Michael addition, 5-exo-dig/5-endo-trig bicyclization and dehydrogenation sequence, resulting in continuous multiple bond-forming events including C-S and C-C bonds to rapidly construct functional organic molecules.

Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes

Indenes and related polycyclic structures have been efficiently synthesized by gold(I)-catalyzed cycloisomerizations of appropriate ortho-(alkynyl)styrenes. Disubstitution at the terminal position of the olefin was demonstrated to be essential to obtain products originating from a formal 5-endo-dig cyclization. Interestingly, a complete switch in the selectivity of the cyclization of o-(alkynyl)-a-methylstyrenes from 6-endo to 5-endo was observed by adding an alcohol to the reaction media. This allowed the synthesis of interesting indenes bearing an all-carbon quaternary center at C1. Moreover, dihydrobenzo[a]fluorenes can be obtained from substrates bearing a secondary alkyl group at the β-position of the styrene moiety by a tandem cycloisomerization/1,2-hydride migration process. In addition, diverse polycyclic compounds were obtained by an intramolecular gold-catalyzed alkoxycyclization of o-(alkynyl)styrenes bearing a nucleophile in their structure. Finally, the use of a chiral gold complex allowed access to elusive chiral 1H-indenes in good enantioselectivities.

Synthesis of chrysene derivatives via copper-catalyzed one-pot dimerization of 2-alkynyl-1-acetylbenzenes

An efficient route for highly substituted chrysene derivatives via operationally simple copper-catalyzed one-pot dimerization of 2-alkynyl-1-acetylbenzenes is described.