76054-73-4

Upstream product

• 501-65-5 diphenyl acetylene 
• 619-04-5 3,4-dimethylbenzoic acid 
• 76054-66-5 (1R,8S)-4,5,11,11-Tetramethyl-1,8,9,10-tetraphenyl-11-germa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene 
• 95-47-6 o-xylene 
• 5182-67-2 1,2-diiodo-4,5-dimethyl-benzene 

Relevant academic research and scientific papers

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.

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.

O-Dihaloarenes as aryne precursors for nickel-catalyzed [2 + 2 + 2] cycloaddition with alkynes and nitriles

o-Dihaloarenes acting as aryne precursors react with acetylenes and nitriles catalyzed by the NiBr2(dppe)/dppe/Zn system to give substituted naphthalene, phenanthridine or triphenylene derivatives depending on the reaction conditions in moderat

7-GERMANORBORNADIENES AND THEIR THERMAL CYCLOELIMINATIONS

7 new 7-germanorbornadienes, crystalline and stable at 25 deg C, have been prepared by Diels-Alder reaction.They decompose thermally via a two step mechanism with an intermediate biradical, forming the benzene derivative and germylenes, R2Ge.