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Upstream product

• 217-59-4 triphenylene 
• 636-98-6 p-nitrobenzene iodide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 591-50-4 iodobenzene 
• 34862-87-8 3'-nitro-[1,1'-biphenyl]-2-amine 
• 615-43-0 2-iodophenylamine 
• 13331-27-6 m-nitrobenzene boronic acid 
• 13029-09-9 2,2'-dibromobiphenyl 
• 24067-17-2 4-nitrophenylboronic acid 
• 583-53-9 2,3-dibromobenzene 
• 5411-56-3 1-(2-bromophenyl)ethanol 
• 2142-69-0 2-bromophenyl methyl ketone 
• 6272-52-2 2-(4-nitrophenyl)aniline 

Relevant academic research and scientific papers

Palladium-catalyzed carbopalladation and carbocyclization of arynes with aryl halides: A highly efficient route to functionalized triphenylenes

Highly substituted triphenylene derivatives were prepared in good yields via the palladium-catalyzed carbocyclization of arynes with aryl iodides. The Royal Society of Chemistry 2006.

Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls

The Pd-catalyzed annulation of arynes by 2-halobiaryls and related vinylic halides provides a very efficient, high yielding synthesis of polycyclic aromatic and heteroaromatic hydrocarbons. This process appears to involve the catalytic, stepwise coupling

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

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.

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.

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.

Method for synthesizing triphenylene compound

The invention provides a method for synthesizing a triphenylene compound represented by a formula (III) shown in the description. The method comprises the steps: dissolving a benzoic acid compound represented by a formula (I) shown in the description, a cyclic iodine onium salt represented by a formula (II) shown in the description, palladium acetate and potassium carbonate in N-methyl pyrrolidone, heating the temperature of the solution to 110 DEG C to 145 DEG C, carrying out a reaction for 6 to 17 hours with stirring, then, subjecting the reacted solution to aftertreatment, thereby obtaining the triphenylene compound. According to the method, the reaction system is simple, the raw materials, particularly the benzoic acid compound are easily obtained, and a substrate is not required to be prepared by multiple steps, so that the reaction yield of the method is relatively high; and the triphenylene is obtained through a one-step reaction between the benzoic acid compound and the cyclic iodine onium salt, so that the reaction route is greatly shortened, and the yield of the obtained corresponding triphenylene compound is 93% to the maximum.

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.