52889-62-0

Usage

Structure

A derivative of biphenyl with an ethynyl group attached to one of the benzene rings.

Industrial applications

Used as a building block for the synthesis of other organic chemicals.

Research and development

Utilized for its unique properties and potential uses in materials science and pharmaceuticals.

Stability

A stable compound.

Safety

No known significant hazards or risks to human health and the environment when handled and used according to standard safety procedures.

Upstream product

• 117417-11-5 (E)-2-Bromo-1-biphenyl-2-ylethene 
• 147492-79-3 1-phenyl-2-{2-(trimethylsilyl)ethynyl}benzene 
• 558-13-4 carbon tetrabromide 
• 1203-68-5 2-Phenylbenzaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 21047-57-4 diethyl (1-diazo-2-oxopropyl)phosphonate 
• 2928-43-0 2-biphenylmethanol 
• 2113-51-1 2-iodobiphenyl 
• 90-41-5 2-phenylaniline 
• 2142-66-7 1-([1,1'-biphenyl]-2-yl)ethanone 
• 7646-93-7 potassium hydrogensulfate 
• 593-92-0 vinylidene dibromide 
• 766-46-1 2-bromo-1-ethynylbenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 3228-74-8 dibenzanthracene-9,14-dione 
• 607731-77-1 2-[(3-methylphenyl)ethynyl]biphenyl 
• 725213-47-8 ethyl 4-(biphenyl-2-ylethynyl)benzoate 
• 85-01-8 phenanthrene 
• 120-12-7 anthracene 
• 1262759-12-5 Br^(1-)*C₄₉H₄₁N₄O⁽¹⁺⁾ 
• 1262759-13-6 Br^(1-)*C₅₁H₄₅N₄O⁽¹⁺⁾ 
• 947-72-8 9-chlorophenanthrene 
• 916588-75-5 2-(3-phenyl-propa-1,2-dienyl)biphenyl 
• 605-05-0 9-benzyl-phenanthrene 

Relevant academic research and scientific papers

Iron-Catalyzed Vinylzincation of Terminal Alkynes

Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of alkyne carbozincation. However, this method suffers from poor tolerance for terminal alkynes, and transformation of the newly introduced organic groups is difficult, which limits its applications. Herein, we report a method for vinylzincation of terminal alkynes catalyzed by newly developed iron catalysts bearing 1,10-phenanthroline-imine ligands. This method provides efficient access to novel organozinc reagents with a diverse array of structures and functional groups from readily available vinylzinc reagents and terminal alkynes. The method features excellent functional group tolerance (tolerated functional groups include amino, amide, cyano, ester, hydroxyl, sulfonyl, acetal, phosphono, pyridyl), a good substrate scope (suitable terminal alkynes include aryl, alkenyl, and alkyl acetylenes bearing various functional groups), and high chemoselectivity, regioselectivity, and stereoselectivity. The method could significantly improve the synthetic efficiency of various important bioactive molecules, including vitamin A. Mechanistic studies indicate that the new iron-1,10-phenanthroline-imine catalysts developed in this study have an extremely crowded reaction pocket, which promotes efficient transfer of the vinyl group to the alkynes, disfavors substitution reactions between the zinc reagent and the terminal C–H bond of the alkynes, and prevents the further reactions of the products. Our findings show that iron catalysts can be superior to other metal catalysts in terms of activity, chemoselectivity, regioselectivity, and stereoselectivity when suitable ligands are used.

Iodine-Catalyzed Methylthiolative Annulation of 2-Alkynyl Biaryls with DMSO: A Metal-Free Approach to 9-Sulfenylphenanthrenes

An iodine-catalyzed sustainable, cost-effective, and atom-economic synthetic methodology is developed to synthesize a wide variety of valuable sulfenylphenanthrenes and polycyclic heteroaromatics in moderate to high yield through electrophilic thiolative annulation of 2-alkynyl biaryls (6-endo-dig cyclization) using methyl sulfoxides such as dimethyl sulfoxide (DMSO) as the sulfur source under transition-metal-free conditions. The transformation requires only iodine in a catalytic amount and trifluoroacetic anhydride. Notably, DMSO played multiple roles such as methylthiolating reagent, oxidant, and solvent in this reaction.

Gold-Catalyzed Synthesis of π-Extended Carbazole-Based Systems and their Application as Organic Semiconductors

Herein we describe a gold-catalyzed bidirectional synthesis of N-heteropolycyclic compounds bearing carbazole moieties – namely π-extended benzodicarbazoles and π-extended indolocarbazoles. Overall, four previously unknown core structures were synthesized. This approach is convergent, modular and the gold-catalyzed key step comprises of a cascade reaction starting from stable di-azido compounds. The obtained molecules were fully characterized and their optical and electronic properties as well as their performance in organic thin-film transistors generated by vacuum deposition were studied. Charge-carrier mobilities of up to 0.3 cm2/Vs were measured. (Figure presented.).

Alumina-Mediated π-Activation of Alkynes

The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.

Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block

A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.

Biphenyl Cyclobutenone Photoelectrocyclizations

In this work, we demonstrate that readily available conjugated bis-aryl cyclobutenones undergo photoelectrocyclization reactions to give the corresponding dihydrophenanthrene cyclobutanones when exposed to 350 nm light, TFA, and TMSCl. We have also found that cyclobutenone electrocyclizations and cycloreversions are in equilibrium.

Metal-Free Synthesis of Selenodihydronaphthalenes by Selenoxide-Mediated Electrophilic Cyclization of Alkynes

A transition-metal-free, selenium mediated electrophilic cyclization reaction was realized through a one-pot procedure between simple alkynes and triflic anhydride-activated selenoxides to give selenium containing dihydronaphthalene products. This method gave good to very high yields for all products, including selenium-substituted phenanthrene, dihydroquinoline, 2H-chromene, and coumarin, which can be further transformed to other functionalized compounds.

SILICON-CONTAINING ELECTRON TRANSPORTING MATERIAL AND ITS APPLICATION

A silicon-containing electron transporting material and its application are disclosed. The silicon-containing electron transporting material employs a silicon-containing compound with a novel structure containing one or more silicon atoms and a specific g

Tertiary amines acting as Alkyl radical equivalents enabled by a P/N heteroleptic Cu(I) photosensitizer

An unprecedented exploration of tertiary amines as alkyl radical equivalents for cross-coupling with aromatic alkynes to access allylarenes has been achieved by a P/N heteroleptic Cu(I)based photosensitizer under photoredox catalysis conditions. Mechanist

Br?nsted Acid-Catalyzed Enantioselective Cycloisomerization of Arylalkynes

The first example of an enantioselective carbocyclization of an alkyne-containing substrate catalyzed by chiral Br?nsted acids was achieved. The use of the 2-hydroxynaphthyl substituent on the alkyne as a directing group constituted the key parameter enabling both efficient regioselective protonation of the carbon–carbon triple bond and chiral induction. The key cationic intermediate could be depicted either as a cationic vinylidene ortho-quinone methide or a stabilized vinyl cation. Atropoisomeric phenanthrenes derivatives were produced in high yields and good enantioselectivities under mild, metal-free reaction conditions in the presence of chiral N-triflylphosphoramide catalysts. The carbenic nature of the cationic intermediate was also exploited to describe an example of alkyne/alkane cycloisomerization.