65673-85-0Relevant academic research and scientific papers
Solid-State Radical C?H Trifluoromethylation Reactions Using Ball Milling and Piezoelectric Materials
Ito, Hajime,Kubota, Koji,Lee, Joo Won,Pang, Yadong
supporting information, p. 22570 - 22576 (2020/10/21)
The application of piezoelectricity for the generation of trifluoromethyl (CF3) radicals is reported together with the development of a method for the mechanochemical C?H trifluoromethylation of aromatic compounds. As compared to conventional solution-based approaches, this mechanoredox C?H trifluoromethylation enables cleaner and more sustainable access to a wide range of trifluoromethylated N-heterocycles and peptides, which are important structural motifs in modern drug discovery. This study thus represents an important milestone for future applications of mechanoredox systems to medicinal and pharmaceutical science.
Palladium-catalyzed C-H ethoxycarbonyldifluoromethylation of electron-rich heteroarenes
Shao, Changdong,Shi, Guangfa,Zhang, Yanghui,Pan, Shulei,Guan, Xiaohong
supporting information, p. 2652 - 2655 (2015/06/16)
The first Pd-catalyzed C-H ethoxycarbonyldifluoromethylation with BrCF2CO2Et has been developed. The use of a bidentate phosphine ligand (Xantphos) is critical for the reaction to occur. A variety of electron-rich heteroarenes, including indoles, furans, thiophenes, and pyrroles, can be ethoxycarbonyldifluoromethylated in moderate to excellent yields. The reactions take place at the C-H bonds adjacent to the heteroatoms with high regioselectivity. This method provides a new protocol for the introduction of difuoroalkyl groups into electron-rich heteroarenes.
Visible light-mediated C-H difluoromethylation of electron-rich heteroarenes
Su, Yi-Ming,Hou, Yu,Yin, Feng,Xu, Yue-Ming,Li, Yan,Zheng, Xiaoqi,Wang, Xi-Sheng
supporting information, p. 2958 - 2961 (2014/06/23)
A novel method for visible-light photoredox-catalyzed difluoromethylation of electron-rich N-, O-, and S-containingheteroarenes under mild reaction conditions is developed. Mechanistic investigation indicates that the net C-H difluoromethylation proceeds through an electrophilic radical-type pathway.
Synthesis of 1-substituted indoles by the vapour phase reaction of N-substituted anilines with glycols and epoxides over a solid catalyst and a vapour phase dealkylation of 1-alkylindole
Nishida, Takuo,Tokuda, Yoshikazu,Tsuchiya, Michihiro
, p. 823 - 830 (2007/10/02)
1-Substituted indoles 4b-h, 5c, e were synthesized in good yields by the vapour phase reaction of N-substituted anilines 1b-e with glycols 2a-c and epoxides 3a, b at 250-400 deg C over a solid catalyst, Neobead P (Al2O3:SiO2:Na2O = 88:9:3), at atmospheric pressure. 1-Alkylindoles 4b, d, g were converted into indole (4a) in good yields by a vapour phase reaction with steam and hydrogen gas over ZnO (10percent) supported on Neobead C (Al2O3) at 500-575 deg C.These reaction pathways are discussed.
Cyclisation indolique selon Bischler en presence d'acides de Lewis
Galons, Herve,Girardeau, Jean-Francois,Farnoux, Claude Combet,Miocque, Marcel
, p. 561 - 564 (2007/10/02)
In a comparative study of various catalysts (hydrochloric acid, Lewis acids) in the Bischler cyclization of α-aminoketones to indoles, aluminium chloride appears as the most active catalyst.Isomerization of β to α-indoles can be observed by raising the reaction temperature.The mechanism seems different from the one frequently suggested by most authors, since it does not affect intermediate aminoketones but indoles.
