1246739-35-4Relevant academic research and scientific papers
Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids
Deng, Guobo,Liang, Yun,Luo, Xiai,Yang, Xiumei,Yang, Yuan,Yang, Yuzhong,Zhou, Liwei
supporting information, p. 1223 - 1230 (2020/04/15)
A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.
Phenanthrene Synthesis by Palladium-Catalyzed Benzannulation with o-Bromobenzyl Alcohols through Multiple Carbon-Carbon Bond Formations
Iwasaki, Masayuki,Araki, Yasuhiro,Nishihara, Yasushi
, p. 6242 - 6258 (2017/06/23)
A palladium-catalyzed benzannulation with o-bromobenzyl alcohols enabled the facile construction of phenanthrene skeletons via the sequential multiple carbon-carbon bond formations. A variety of multisubstituted phenanthrenes were synthesized by the reaction of (Z)-β-halostyrenes with o-bromobenzyl alcohols as well as by the three-component coupling of alkynes, aryl bromides, and o-bromobenzyl alcohols. The electron-deficient phosphine ligand played an important role to control the sequential oxidative addition of two different organic halides employed, which realized the selective formation of the desired phenanthrenes in good yields. This synthetic protocol was also applicable to the synthesis of the highly fused polycyclic aromatic hydrocarbons such as tetraphenes.
Manganese(III) acetate-mediated cyclization of diarylmethylenecyclopropa[ b ]naphthalenes: A method for the synthesis of 1,2-benzanthracene derivatives
Cao, Jian,Miao, Maozhong,Chen, Wanli,Wu, Luling,Huang, Xian
, p. 9329 - 9337 (2011/12/15)
The manganese(III) acetate-mediated free radical cyclization of diarylmethylenecyclopropa[b]naphthalenes with nucleophiles such as carboxylic acid and sulfonic acid provides an efficient method for the synthesis of 1,2-benzanthracenes in moderate to good yields under mild conditions. In addition, after several steps of simple and routine operations, the obtained 1,2-benzanthracenes bearing an acetoxy group could be easily converted to structurally more sophisticated 1,2-benzanthracene derivatives, which are not easily accessible yet potentially useful candidates for materials science.
Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation
Wang, Congyang,Rakshit, Souvik,Glorius, Frank
supporting information; experimental part, p. 14006 - 14008 (2010/12/24)
A novel protocol for palladium-catalyzed intermolecular formal [4 + 2] annulation of 2-phenylbenzoic acids with alkynes is described. Acridine is shown to be essential for the high reaction efficiency. Phenanthrene derivatives are formed in moderate to good yields without coupling (pseudo)halides or organometallic species.
