25634-84-8

Upstream product

• 636-31-7 1,2,4,5-tetraiodobenzene 
• 536-74-3 phenylacetylene 
• 120-80-9 benzene-1,2-diol 
• 108-46-3 recorcinol 
• 2563-26-0 4,5-dibromobenzene-1,2-diol 
• 61524-51-4 2,4-dibromo-5-hydroxyphenol 
• 14753-51-6 2,5-dibromohydroquinone 
• 123-31-9 hydroquinone 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 95-94-3 1,2,4,5-tetrachlorobenzene 

Downstream Products

• 25634-89-3 12,14-diphenyldiindeno[2,1-a:1',2'-h]-s-indacene 
• 25634-90-6 5,12-Diphenyl-(diindeno-<2.1-a;1.2-g>-S-indacen) 

Relevant academic research and scientific papers

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.

Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors

The gold-catalyzed facile synthesis of U-shaped and S-shaped bispentalenes is described from easily available tetra(arylethynyl)-benzenes and -naphthalenes. The optoelectronic and transistor properties were also investigated. The selectivity between the U-shaped and S-shaped bispentalene isomers can be tuned by the bulkiness of the ligand and the substrates. The S-shaped naphthalene-based bispentalene shows a one-dimensional face-to-face packing pattern in solid state and a good hole mobility, indicating that the S-shaped bispentalene core is highly suitable for transistor applications. The gold-catalyzed annulation of tetraynes provides a useful protocol in the synthesis of bispentalenes for organic semiconductors.

Synthesis of phenylethynylbenzenes

A method of: reacting a dihydroxybenzene with bromine to form a bromodihydroxybenzene; reacting the bromodihydroxybenzene with trifluoromethanesulfonyl chloride or trifluoromethanesulfonic anhydride to form a bromotrifluoromethanesulfonatobenzene; and reacting the bromotrifluoromethanesulfonatobenzene with phenylacetylene to form a phenylethynylbenzene.

Tetraalkynylated and tetraalkenylated benzenes and pyridines: Synthesis and photophysical properties

Tetra(arylalkynyl)pyridines and tetra(arylalkenyl)pyridines and their benzene analogues were prepared by palladium-catalyzed cross-coupling reactions from the commercially available chlorinated substrates in good to excellent yields. The photophysical pro

Palladium-catalyzed copper-free sonogashira coupling reaction in water and acetone

An efficient palladium-catalyzed copper-free Sonogashira reaction in water and acetone has been developed under mild conditions. The results showed that the aryl iodides could carry out the cross-coupling reaction with a variety of terminal alkynes in high yields in water-acetone in the absence of amine, copper(I) salts, or phosphine ligands at 60°C for one hour, and good yields were obtained for aryl bromides at 60°C for 12-24 hours in the presence of triphenylphosphine and piperidine. The method could be used to synthesize polyethynyl aromatic compounds in a one-pot reaction. Georg Thieme Verlag Stuttgart.

Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both hom

The Third-order Optical Non-linearity of the Phenylethynyl-substituted Benzene System

Phenylethynyl substituted benzenes 1, 2 and 3 are synthesized by the Pd-coupling reaction of phenylacetylene with the corresponding bromobenzene; the third-order optical non-linearity (3)(ω)> increases with the participation of ?-conjugation

Palladium-Catalyzed Alkenylation and Alkynylation of Polyhaloarenes

Alkenylation of several polyhaloarenes proceeded in low to moderate yields.Iodo groups could be reacted selectively in the presence of bromo groups; however, no more than two alkenyl groups could be introduced on contiguous, aromatic carbons.Alkynylation