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Upstream product

• 588-16-9 m-methoxyacetanilide 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 579-75-9 2-Methoxybenzoic acid 
• 501-65-5 diphenyl acetylene 
• 578-57-4 2-bromoanisole 
• 10365-98-7 3-methoxyphenylboronic acid 
• 100-66-3 methoxybenzene 

Relevant academic research and scientific papers

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.

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

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 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.

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.