138768-49-7Relevant academic research and scientific papers
Synthesis of Aryl Alkynes via Copper Catalyzed Decarboxylative Alkynylation of 2-Nitrobenzoic Acids
Yu, Yongqi,Chen, Xiang,Wu, Qianlong,Liu, Da,Hu, Liang,Yu, Lin,Tan, Ze,Gui, Qingwen,Zhu, Gangguo
supporting information, p. 8556 - 8566 (2018/06/29)
An efficient protocol for the synthesis of internal aryl alkynes was achieved via Cu-catalyzed decarboxylative cross-coupling reactions, and to the best of our knowledge, this is the first example of a Cu-catalyzed decarboxylative alkynylation of benzoic acids with terminal alkynes. This approach utilizes simple Cu salt as catalyst and O2, an abundant, clean, and green material, as the oxidant. The reaction tolerates various functional groups, and a variety of internal aryl alkynes were synthesized in 46-83% yields.
A highly effective one-pot synthesis of quinolines from 2-alkynylnitrobenzenes
Okuma, Kentaro,Ozaki, Saori,Seto, Jun-Ichi,Nagahora, Noriyoshi,Shioji, Kosei
experimental part, p. 935 - 942 (2010/09/18)
A highly effective one-pot synthesis of poly-substituted quinolines from 2-alkynylnitrobenzenes using inexpensive reagents has been developed. Reaction of 2-alkynylnitrobenzenes with Sn/HCl in EtOH resulted in the formation of 2-aminophenyl ketones and subsequently condensed in situ with ketones to form tri-substituted quinolines in 80-97% yields.
Cyclopentadienyliron-mediated introduction of functionalized alkyl or alkynyl groups to arenes in an addition-demetallation sequence
Sutherland, Ronald G.,Zhang, Chunhao,Piorko, Adam
, p. 357 - 373 (2007/10/02)
Nitromethyl, cyanomethyl, and phenylethynyl anions add selectively ortho to arenes containing electron-withdrawing groups and complexed with cyclopentadienyliron.Under similar reaction conditions anions such as alkyl, dichloromethyl and trichloromethyl add in a non-selective way.Addition of the trichloromethyl anion is thermodynamically controlled at extended reaction times and, due to the size of the anion, the meta addition is favoured.Demetallation of adducts leads to ortho-nitromethylated, cyanomethylated or phenylethynylated arenes, respectively.With symmetrical arene complexes the addition-demetallation sequence leads to the introduction of a trichloromethyl group into the arene ring, yielding a single product.A one-pot procedure for trichloromethylation of dialkylarenes starting from appropriate cyclopentadienyliron complexes gives β-trichloromethylated dialkylarenes in a good yield.
