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Upstream product

• 3010-81-9 tris(4-methoxyphenyl)methanol 
• 501-65-5 diphenyl acetylene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 696-62-8 para-iodoanisole 
• 579-75-9 2-Methoxybenzoic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 10365-98-7 3-methoxyphenylboronic acid 
• 100-66-3 methoxybenzene 
• 51-66-1 4-methoxyacetanilide 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 

Relevant academic research and scientific papers

Polyaromatic Products of Three-Component Coupling of Aryl Halide with Two Molecules of Arylacetylene and Arylboronic Acid under Ligand-Free Catalysis Conditions

The aryl halide-arylacetylene-arylboronic acid three-component coupling in the presence of a Pd catalyst containing no organic ligands is described. The reaction routes that take place in the reaction system are shown to include the consecutive carbopalla

Synthesis of Benzo-Fused Cyclic Compounds via Rhodium-Catalyzed Decarboxylative Coupling of Aromatic Carboxylic Acids with Alkynes

The decarboxylative coupling of diversely substituted benzoic acids with internal alkynes proceeds smoothly in the presence of a [RhCl(cod)] 2/1,2,3,4-tetraphenyl-1,3-cyclopentadiene catalyst system to selectively produce highly substituted nap

Iridium(III)-Catalyzed Dehydrogenative Coupling of Salicylic Acids with Alkynes: Synthesis of Highly Substituted 1-Naphthol Derivatives

The iridium(III)-catalyzed dehydrogenative coupling of salicylic acids with diarylacetylenes proceeds smoothly accompanied by decarboxylation to produce 5,6,7,8-tetraarylnaphthalen-1-ols selectively. This reaction can be conducted even without addition of external oxidant. The same kind of naphthalen-1-ol derivative can also be synthesized predominantly by the reaction of 4-hydroxybenzoic acid with diphenylacetylene. Some of naphthalen-1-ols prepared exhibits unique optical properties.

Room Temperature Decarboxylative and Oxidative [2+2+2] Annulation of Benzoic Acids with Alkynes Catalyzed by an Electron-Deficient Rhodium(III) Complex

It has been established that an electron-deficient (η5-cyclopentadienyl)rhodium(III) [CpERhIII] complex is capable of catalyzing the decarboxylative and oxidative [2+2+2] annulation of benzoic acids with alkynes to produce substituted naphthalenes at room temperature. The appropriate choice of the additive and the solvent is crucial for this transformation. This catalyst system allowed use of oxygen as a terminal oxidant and broadened the substrate scope including both aromatic and aliphatic alkynes. In this catalysis, the electron deficient nature of the CpERhIII catalyst would cause the strong rhodium-π interaction, which accelerates the decarboxylation as well as the C?H bond cleavage.

Solvent free, phosphine free Pd-catalyzed annulations of aryl bromides with diarylacetylenes

Palladium nanoparticles and sodium acetate catalyze the reaction of aryl bromide with diarylacetylene to produce annulated products in good yield. One equivalent of PEG-600 serves as the solvent. This procedure is compatible with a wide variety of functional groups.

Synthesis of polysubstituted naphthalenes by iron-catalyzed [2+2+2] annulation of grignard reagents with alkynes

Iron catalyzes the oxidative [2+2+2] annulation of an arylmagnesium compound with two molecules of an internal alkyne via C-H bond activation at 0 °C to produce polysubstituted naphthalene. Georg Thieme Verlag Stuttgart.New York.

Synthesis of highly substituted acenes through rhodium-catalyzed oxidative coupling of arylboron reagents with alkynes

The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids or their esters with alkynes smoothly proceed to produce the corresponding annulated products. Of special note, highly substituted, readily soluble, and tractable anthracene and tetracene derivatives can be obtained selectively from 2-naphthyl- and 2-anthrylboron reagents, respectively.

Synthesis of highly substituted naphthalene and anthracene derivatives by rhodium-catalyzed oxidative coupling of arylboronic acids with alkynes

The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids with alkynes effectively proceeds in the presence of a copper-air oxidant to produce the corresponding annulated products. Of special note, anthracene derivatives can be obtained

Palladium-catalyzed formation of highly substituted naphthalenes from arene and alkyne hydrocarbons

Several highly substituted naphthalenes 3 have been synthesized in a one-pot reaction by treatment of arenes 1 with alkynes 2 in the presence of palladium acetate and silver acetate. In this Pd-catalyzed protocol, an arene provides a benzo source for the construction of a naphthalene core through twofold aryl C - H bond activation. Reaction of triphenylphosphine with diphenylethyne (2 a) under the catalysis of PdIV complexes produced 1,2,3,4-tetraphenylnaphthalene (3ba) in 62% yield. Here, triphenylphosphine undergoes one aryl C - P bond cleavage and one aryl C - H bond activation to serve as a benzo moiety. Crystal structures of cycloadducts 3ea, 3ga, and 3ac have been analyzed. The twisted naphthalenes arise not only from the overcrowded substituents but also from the contribution of the CH3-π interaction.

Rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes via successive C-H and C-C bond cleavages

(Chemical Equation Presented) The rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes effectively proceeds in a 1:2 manner via cleavage of C-H and C-C bonds to produce the corresponding naphthalene derivatives. Addition of trior tetraphenylcyclopentadiene as a ligand is crucial for the reaction to occur efficiently.