19027-67-9Relevant academic research and scientific papers
Rhodaelectrocatalysis for Annulative C?H Activation: Polycyclic Aromatic Hydrocarbons through Versatile Double Electrocatalysis
Kong, Wei-Jun,Finger, Lars H.,Oliveira, Jo?o C. A.,Ackermann, Lutz
supporting information, p. 6342 - 6346 (2019/04/08)
Rapid access to structurally diversified polycyclic aromatic hydrocarbons (PAHs) in a controlled manner is of key significance in materials sciences. Herein, we describe a strategy featuring two distinct electrocatalytic C?H transformations for the synthesis of novel nonplanar PAHs. The combination of rhodaelectrooxidative C?H activation/[2+2+2] alkyne annulation of easily accessible boronic acids with electrocatalytic cyclodehydrogenation provided modular access to diversely substituted PAHs with electricity as a sustainable oxidant. The unique molecular topology as well as the photophysical and electronic properties of the thus obtained PAHs were fully analyzed. The unique power of this metallaelectrocatalysis method was demonstrated by the chemoselective assembly of synthetically useful iodo-substituted PAHs.
Synthesis of highly substituted acenes through rhodium-catalyzed oxidative coupling of arylboron reagents with alkynes
Fukutani, Tatsuya,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
scheme or table, p. 2867 - 2874 (2011/05/28)
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
Wu, Yao-Ting,Huang, Ke-Hsin,Shin, Chien-Chueh,Wu, Tsun-Cheng
experimental part, p. 6697 - 6703 (2009/07/01)
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.
