1165-53-3

Usage

Uses

Used in Organic Synthesis:
1,2,4-Triphenylbenzene is used as a building block in organic synthesis for the creation of complex organic molecules. Its versatile structure allows for the formation of various chemical compounds, making it a valuable component in the synthesis process.
Used in Dye and Pigment Manufacturing:
1,2,4-Triphenylbenzene is used as a key component in the manufacturing of dyes and pigments. Its aromatic structure contributes to the color and stability of these products, making it an essential ingredient in the production of high-quality dyes and pigments.
Used in Pharmaceutical Industry:
1,2,4-Triphenylbenzene is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties enable the development of new drugs with potential therapeutic applications.
Used in Material Science:
1,2,4-Triphenylbenzene is used as a valuable tool in the field of material science. Its potential applications include the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices. Its unique structure and properties make it an important compound in the advancement of materials and the study of organic chemistry.

Upstream product

• 51092-02-5 2,5-bis(phenyl)-thiophene-1,1-dioxide 
• 536-74-3 phenylacetylene 
• 54119-53-8 3,4-diphenylthiopnene 1,1-dioxide 
• 115228-64-3 2,3,5-triphenyl-benzoic acid 
• 5587-78-0 4-hydroxy-3,4-diphenylcyclopent-2-en-1-one 
• 33441-42-8 4-amino-3,5,6-triphenyl-Δ¹-cyclohexene 
• 78486-55-2 2,5-diiodobiphenyl 
• 100-47-0 benzonitrile 
• 3907-06-0 3,3-Dimethylcyclopropen 
• 75-05-8 acetonitrile 
• 19682-74-7 1,3,6-Triphenylhexa-1,3,5-trien 
• 201230-82-2 carbon monoxide 
• 140-88-5 ethyl acrylate 
• 60631-83-6 4’-Bromo-[1,1’:3’,1”]terphenyl 

Downstream Products

• 612-71-5 1,3,5-triphenylbenzene 
• 3073-03-8 2-phenyltriphenylene 

Relevant academic research and scientific papers

First examples of homogeneous catalytic cyclotrimerization and polymerization of phenylacetylene and copolymerization of phenylacetylene and norbonene with dinuclear complexes containing unbridged metal-metal quadruple bond

First examples of application of dinuclear complexes containing unbrigded metal-metal quadruple bond as catalysts in cyclotrimerization, oligomerization and polymerization of substituted acetylene are reported. The d4-d4 dinuclear co

Enhanced Catalytic Activity of Nickel Complexes of an Adaptive Diphosphine-Benzophenone Ligand in Alkyne Cyclotrimerization

Adaptive ligands, which can adapt their coordination mode to the electronic structure of various catalytic intermediates, offer the potential to develop improved homogeneous catalysts in terms of activity and selectivity. 2,2′-Diphosphinobenzophenones have previously been shown to act as adaptive ligands, the central ketone moiety preferentially coordinating reduced metal centers. Herein, the utility of this scaffold in nickel-catalyzed alkyne cyclotrimerization is investigated. The complex [(p-tolL1)Ni(BPI)] (p-tolL1 = 2,2′-bis(di(para-tolyl)phosphino)-benzophenone; BPI = benzophenone imine) is an active catalyst in the [2 + 2 + 2] cyclotrimerization of terminal alkynes, selectively affording 1,2,4-substituted benzenes from terminal alkynes. In particular, this catalyst outperforms closely related bi- and tridentate phosphine-based Ni catalysts. This suggests a reaction pathway involving a hemilabile interaction of the C-O unit with the nickel center. This is further borne out by a comparative study of the observed resting states and DFT calculations.

Solvent-free oligomerization of phenylacetylene catalyzed by (cyclopentadienyl)nickel complexes

The solvent-free reaction of phenylacetylene at 115°C in the presence of nickelocene, [(η-Cp)Ni]2(PhC≡CH), [(η-Cp)Ni(CO)]2, (η-Cp)Ni(NO), (η-Cp)Ni(GeBr3)(CO), (η-Cp)Ni[(P(OMe3)]Cl, (η-Cp)Ni(Ph3P)Cl, (η-Cp)Ni(Bu3nP)I, or (Ph3P)2Ni(CO)2 gives rise to a mixture of cyclotrimers, linear oligomers and poly(phenylacetylene), no reaction being observed in the case of internal acetylenes. Cyclotrimer formation is favoured by the presence of (a) added phosphine (2 equiv.), or (b) (cyclopentadienyl)nickel catalysts bearing a chloro substituent at Ni. A reduction in reaction temperature results in lower conversion but favours linear oligomer and polymer formation. The extent of reaction is greatly reduced in the case of (a) nickelocene in the presence of 2 equiv. PBu3n, (b) (η-Cp)Ni(GeBr3)(CO), or (c) (η-Cp)Ni(NO). The main effect of the presence of solvent, regardless of whether it is potentially coordinating (toluene) or not (n-octane), is to suppress almost completely reactions catalyzed by nickelocene. The Royal Society of Chemistry 2000.

Rh-POP pincer Xantphos complexes for C-S and C-H activation. Implications for carbothiolation catalysis

The neutral Rh(I)-Xantphos complex [Rh(κ3-P,O,P-Xantphos)Cl]n, 4, and cationic Rh(III) [Rh(κ3-P,O,P-Xantphos)(H)2][BArF4], 2a, and [Rh(κ3-P,O,P-Xantphos-3,5-C6H3(CF3)2)(H)2][BArF4], 2b, are described [ArF = 3,5-(CF3)2C6H3; Xantphos = 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Xantphos-3,5-C6H3(CF3)2 = 9,9-dimethylxanthene-4,5-bis(bis(3,5-bis(trifluoromethyl)phenyl)phosphine]. A solid-state structure of 2b isolated from C6H5Cl solution shows a κ1-chlorobenzene adduct, [Rh(κ3-P,O,P-Xantphos-3,5-C6H3(CF3)2)(H)2(κ1-ClC6H5)][BArF4], 3. Addition of H2 to 4 affords, crystallographically characterized, [Rh(κ3-P,O,P-Xantphos)(H)2Cl], 5. Addition of diphenyl acetylene to 2a results in the formation of the C-H activated metallacyclopentadiene [Rh(κ3-P,O,P-Xantphos)(ClCH2Cl)(σ,σ-(C6H4)C(H)=CPh)][BArF4], 7, a rare example of a crystallographically characterized Rh-dichloromethane complex, alongside the Rh(I) complex mer-[Rh(κ3-P,O,P-Xantphos)(η2-PhCCPh)][BArF4], 6. Halide abstraction from [Rh(κ3-P,O,P-Xantphos)Cl]n in the presence of diphenylacetylene affords 6 as the only product, which in the solid state shows that the alkyne binds perpendicular to the κ3-POP Xantphos ligand plane. This complex acts as a latent source of the [Rh(κ3-P,O,P-Xantphos)]+ fragment and facilitates ortho-directed C-S activation in a number of 2-arylsulfides to give mer-[Rh(κ3-P,O,P-Xantphos)(σ,κ1-Ar)(SMe)][BArF4] (Ar = C6H4COMe, 8; C6H4(CO)OMe, 9; C6H4NO2, 10; C6H4CNCH2CH2O, 11; C6H4C5H4N, 12). Similar C-S bond cleavage is observed with allyl sulfide, to give fac-[Rh(κ3-P,O,P-Xantphos)( η3-C3H5)(SPh)][BArF4], 13. These products of C-S activation have been crystallographically characterized. For 8 in situ monitoring of the reaction by NMR spectroscopy reveals the initial formation of fac-κ3-8, which then proceeds to isomerize to the mer-isomer. With the para-ketone aryl sulfide, 4-SMeC 6H4COMe, C-H activation ortho to the ketone occurs to give mer-[Rh(κ3-P,O,P-Xantphos)(σ,κ1-4-(COMe)C6H3SMe)(H)][BArF4], 14. The temporal evolution of carbothiolation catalysis using mer-κ3-8, and phenyl acetylene and 2-(methylthio)acetophenone substrates shows initial fast catalysis and then a considerably slower evolution of the product. We suggest that the initially formed fac-isomer of the C-S activation product is considerably more active than the mer-isomer (i.e., mer-8), the latter of which is formed rapidly by isomerization, and this accounts for the observed difference in rates. A likely mechanism is proposed based upon these data.

One-pot synthesis of multisubstituted quaterphenyls and cyclopropanes

An efficient one-step synthetic route toward multifunctionalized quaterphenyls 3 or cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a regioselective [3C+3C] or [1C+2C] annulation. The reaction features mild conditions, multisubstitution, and functional groups tolerance and is transition metal catalyst-free. The protocol provides a novel alternative to the conventional methodologies for the synthesis of quaterphenyls or cyclopropanes.

Catalytic performance of tantalum-η2-alkyne complexes [TaCl3(R1C≡CR2)L2] for alkyne cyclotrimerization

Structurally characterized tantalum-η2-alkyne complexes [TaCl3(η2-EtC=CEt)L2] (1, L2 = 1,2-dimethoxyethane (DME); 2, L = py) acted as catalysts for the cyclotrimerization of terminal alkynes. The catalytic reaction proceeded at 25 °C within few hours and the trisubstituted benzenes were obtained without the formation of linear oligomers. A new tantalum complex having a terminal alkyne ligand, [TaCl3(η2-Me3SiC≡ CH)(dme)l (3), was prepared, and its catalytic performance was also investigated.

Regioselective Cyclotrimerization of Terminal Alkynes Using a Digermyne

The catalytic activation of small neutral molecules followed by the formation of C?C bonds is a highly important method to increase the complexity and/or value of simple starting materials. Reported is an isolable digermyne, a compound with a Ge≡Ge bond, which acts as a precatalyst for the cyclotrimerization of terminal arylacetylenes to afford the corresponding 1,2,4-triarylbenzenes with absolute regioselectivity. The results demonstrate that bespoke main-group-element compounds can catalytically activate and transform small neutral organic molecules and induce the formation of C?C bonds.

New Substituted Cyclopentenones by Coupling of Pauson-Khand and Michael-type Reactions

A new catalytic synthesis of substituted cyclopentenones from alkynes, alkenes bearing an electron-withdrawing group and CO in the presence of Co2(CO)8 is reported.It consists of a coupled process involving Pauson-Khand and Michael-type reactions.The formation of cyclopentenone derivatives is strongly dependent on the nature of the alkyne and of the activated alkene.

Reactivity of dimetallapentaboranes-nido- [Cp2*M2B3H7]-with alkynes: Insertion to form a ruthenacarborane (M = RuH) versus catalytic cyclotrimerization to form arenes (M = Rh)

Catalysis with clusters: Transition metal characteristics control metallaborane reactivity as demonstrated by the reaction of a pair of isoelectronic and nearly isostructural metallaboranes with substituted alkynes. Novel catalytic chemistry of nido-[1,2-(Cp*Rh)2B3H7] and nido-[2,3-(Cp*Rh)2B3H7] (shown) with alkynes (see scheme) is observed with activities and selectivities that depend on catalyst structure and the alkyne substituents.

Ni-catalyzed cross-coupling reaction of aryl chlorides with arylboronic acids in IPA without using a reducing reagent

The coupling reaction of aryl chlorides with arylboronic acids was successfully performed in isopropanol (IPA) by using [NiCl(Ph2PCH2CH2OH)2(H2O)]Cl (5), a cationic Ni(II)-complex, as a precatalyst in the absence of a reducing agent. The coupling reaction proceeded smoothly under mild conditions to provide biaryls in satisfactory to excellent yields, and formation of the undesired dechlorination products of aryl chlorides was completely prevented.