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InChI:InChI=1/C19H14/c1-13-7-6-12-18-16-9-3-2-8-14(16)15-10-4-5-11-17(15)19(13)18/h2-12H,1H3

Upstream product

• 68151-17-7 3,4-dihydrotriphenylen-1(2H)-one 
• 103440-11-5 1',2'-Epoxy-2-o-tolyl-bicyclohexyl-2-ol 
• 854641-48-8 (+/-)-1-hydroxy-1-methyl-1.2.3.4.9.10.11.12-octahydro-triphenylene 
• 6580-35-4 3,4,9,10,11,12-hexahydro-2H-triphenylen-1-one 
• 932-31-0 ortho-tolylmagnesium bromide 
• 1502-22-3 2-(1-cyclohexenyl)cyclohexanone 
• 109937-28-2 2-cyclohex-1-enyl-1-o-tolyl-cyclohexanol 
• 1310338-13-6 C₁₉H₁₅F 
• 39655-09-9 2-iodo-2’-methylbiphenyl 
• 7073-69-0 2-(2-bromophenyl)propanol 
• 40508-78-9 2-iodo-3’-methylbiphenyl 
• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 132-65-0 dibenzothiophene 
• 29829-22-9 S-methyldibenzothiophenium tetrafluoroborate 

Relevant academic research and scientific papers

Annulative π-Extension of Unactivated Benzene Derivatives through Nondirected C-H Arylation

Annulative π-extension chemistry provides a concise synthetic route to polycyclic arenes. Herein, we disclose a nondirected annulation approach of unactivated simple arenes. The palladium-catalyzed 2-fold C-H arylation event facilitates tandem C-C linkage relays to furnish fully benzenoid triphenylene frameworks using cyclic diaryliodonium salts. The inseparable regioisomeric mixture of 1- and 2-methyltriphenylenes is identified by the combined analysis of ion mobility-mass spectrometry, gas-phase infrared spectroscopy, and molecular simulation studies.

Two-in-One Strategy for the Pd(II)-Catalyzed Tandem C-H Arylation/Decarboxylative Annulation Involved with Cyclic Diaryliodonium Salts

We report here a two-in-one strategy for the Pd(II)-catalyzed tandem C-H arylation/decarboxylative annulation between readily available cyclic diaryliodonium salts and benzoic acids. The carboxylic acid functionality can be used as both a directing group for the ortho-C-H arylation and the reactive group for the tandem decarboxylative annulation. By a step-economical double cross-coupling annulation procedure, the privileged triphenylene frameworks were efficiently constructed, which have potential applications in material chemistry.

Synthesis of triphenylene derivatives by Pd-catalyzed Suzuki coupling/intramolecular C–H activation between arylboronic acids and dibromobiphenyls

An efficient and regioselective synthesis of functionalized triphenylenes via palladium-catalyzed Suzuki-Miyaura coupling and subsequent intramolecular C–H activation between arylboronic acids and dibromobiphenyls was developed. This methodology showed excellent atomic economy and regiospecificity as well as synthetic feasibility of unsymmetrical triphenylenes.

Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C-H Activation and Decarboxylation

A novel tandem intermolecular decarboxylative coupling reaction of o-bromobenzoic acids and aryl iodides has been developed. The method affords a range of unsymmetrically triphenylenes and displays unique regioselectivity and broad substrate scope. Mechanistically, palladium/norbornene-catalyzed C-H activation and subsequent double decarboxylative coupling reactions were involved. Moreover, the triphenylenes can also be synthesized from 2-iodobiphenyls and o-bromobenzoic acids under norbornene-free conditions.

Desulfurization of dibenzothiophene and dibenzothiophene sulfone via Suzuki–Miyaura type reaction: Direct access to o-terphenyls and polyphenyl derivatives

The reactivity of dibenzothiophene (DBT) or dibenzothiophene sulfone (DBTO2) with a variety of phenylboronic acids was mediated by the nickel precursor [Ni(dippe)Cl2] in the presence of a base. The reaction was performed under relatively mild conditions (70–100 °C), in aqueous media. The study of the reactivity revealed the role of water as a hydrogen source and showed a competition between the desulfurization of the corresponding substrates via a hydrodesulfurization (HDS) or by a hydrodesulfurative cross-coupling (HDSCC) reaction. Furthermore, in the absence of water sulfur-free poly-phenylic compounds were obtained in good yields as a result of a Suzuki–Miyaura type reaction, being the main product in most of the cases the corresponding o-terphenyl derivative, these products are valuable building blocks in the synthesis of more complex materials.

Synthesis of Functionalized Triphenylenes via a Traceless Directing Group Strategy

A novel ligand-free Pd-catalyzed cascade reaction between o-chlorobenzoic acids and cyclic diaryliodonium salts is reported. This one-pot procedure involves a carboxylic acid directed o-arylation followed by intramolecular decarboxylative annulation affording various valuable triphenylenes, which can be further transformed into diversified building blocks for material chemistry. For the first time, it was shown that an aromatic halide can react with diaryliodonium salts under the direction of carboxylic acid functionality. It was also demonstrated that the carboxylic acid could be employed as both a traceless directing group and functional handle for the atom- and step-economical one-pot double cross-coupling annulation reaction with cyclic diaryliodonium salts as the π-extending agents.

Palladium Catalyzed C-I and Vicinal C-H Dual Activation of Diaryliodonium Salts for Diarylations: Synthesis of Triphenylenes

Using the synthetic strategy of palladium-catalyzed dual activation of both C-I and vicinal C-H bonds of diaryliodonium salts, we report an approach for direct diarylations of 2-bromobiphenyls or bromobenzenes. As a result, a wide range of triphenylenes with various substituents have been synthesized in good yields. These triphenylenes are expected to be employed in the "bottom-up" synthesis of functional aromatic molecules in material science.

C-C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and Application in the Assembly of Polycyclic Aromatic Hydrocarbons

Herein, we disclose a new and efficient synthetic approach to triphenylene-based polycyclic aromatic hydrocarbons (PAHs) from ring-fused benzocyclobutenols (RBCBs) through the cleavage of the C-C σ-bond. Two key transformations are involved: (a) palladium-catalyzed C-C bond (hetero)arylation of RBCBs; and (b) Lewis acid-promoted intramolecular annulation leading to complex polycyclic compounds. A variety of multiply substituted triphenylenes and derivatives are obtained in synthetically useful yields.

Synthetic method for 9,10-benzophenanthrene compound

The invention discloses a synthetic method for a 9,10-benzophenanthrene compound. The synthetic method comprises the following concrete steps: dissolving a compound as shown in a formula (2) which is described in the specification and another compound as shown in a formula (4) which is described in the specification in N,N-dimethyl formamide under the protection of inert gas; and carrying out a reaction at 120 to 140 DEG C under the action of copper trifluoromethanesulfonate, sodium carbonate and caesium acetate so as to obtain the 9,10-benzophenanthrene compound as shown in a formula (I) which is described in the specification. According to the invention, 2-bromobiphenyl is used as a raw material, diaryl iodate is used as an arylation reagent, bivalent copper is used as a catalyst, and sodium carbonate and caesium acetate are used as mixed base; the synthetic method has the characteristics of usage of easily available raw materials, short reaction time, high yield, etc.; and as a simplest graphene monomer, the synthesized 9,10-benzophenanthrene compound good application prospects in the field of organic photoelectricity.

Synthesis of Triphenylenes Starting from 2-Iodobiphenyls and Iodobenzenes via Palladium-Catalyzed Dual C-H Activation and Double C-C Bond Formation

A novel and facile approach for the synthesis of triphenylenes has been developed via palladium-catalyzed coupling of 2-iodobiphenyls and iodobenzenes. The reaction involves dual palladium-catalyzed C-H activations and double palladium-catalyzed C-C bond formations. A range of unsymmetrically functionalized triphenylenes can be synthesized with the reaction. The approach features readily available starting materials, high atom- and step-economy, and access to various unsymmetrically functionalized triphenylenes.