1609653-19-1Relevant academic research and scientific papers
Copper-catalyzed aminotrifluoromethylation of unactivated alkenes with (TMS)CF3: Construction of trifluoromethylated azaheterocycles
Lin, Jin-Shun,Liu, Xiang-Geng,Zhu, Xiao-Long,Tan, Bin,Liu, Xin-Yuan
, p. 7084 - 7092 (2014)
The first example of a copper(I)-catalyzed intramolecular aminotrifluoromethylation of unactivated alkenes using (TMS)CF3 (trimethyl(trifluoromethyl)silane) as the CF3 source is described. A broad range of electronically and structurally varied substrates undergo convenient and step-economical transformations for the concurrent construction of a five- or six-membered ring and a C-CF3 bond toward different types of trifluoromethyl azaheterocycles. The methodology not only circumvents use of expensive electrophilic CF3 reagents or the photoredox strategy but also expands the scope to substrates that are difficult to access by the existing methods. Mechanistic studies are conducted, and a plausible mechanism is proposed.
Synthesis method of photocatalytic fluoroalkyl indoline
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Paragraph 0025-0026; 0029-0042, (2020/06/02)
The invention discloses a synthesis method of photocatalytic fluoroalkyl indoline. The synthesis method comprises the following steps: step 1, taking a 2-allyl aniline compound as a raw material, taking RF source as a fluorinating reagent for providing a fluorine source, taking Blue LEDs as a light source, taking Eosin Y Na as a photocatalyst, taking TMEDA as an alkali additive, and reacting in asolvent MeCN/H2O; step 2, extracting the reaction product, combining organic phases, drying, filtering, and concentrating under reduced pressure to obtain a crude product; and step 3, further carryingout chromatographic purification on the crude product to obtain a target product, namely fluoroalkyl indoline. The invention has the following beneficial effects: visible light is a cheap, clean andpollution-free green energy source; MeCN/H2O is used as a mixed solvent, so that the method conforms to the concept of green chemistry, and is environment-friendly, simple in post-treatment and simpleand convenient to operate; and the reaction device is simple, reaction conditions are mild, the sytnhesis can be realized at room temperature, energy consumption is saved, and high yield of the target product can be achieved.
Copper-Promoted Intramolecular Aminotrifluoromethylation of Alkenes with Langlois Reagent as the Trifluoromethyl Source
Zhang, Hong-Yu,Huo, Wenge,Ge, Chao,Zhao, Jiquan,Zhang, Yuecheng
supporting information, p. 962 - 965 (2017/05/05)
A novel approach for copper-promoted intramolecular aminotrifluoromethylation of alkenes using inexpensive CF3SO2Na as the trifluoromethyl source is described. The feature of this method is the concurrent construction of a five-membered ring and a C-CF3 bond in the simple copper salt/TBHP system. A gram-scale reaction was tested with a slight decrease in the yield. This protocol provides an operationally simple, step-economical and synthetically useful access to a variety of trifluoromethyl indolines, pyrrolidines and lactams.
Efficient copper-catalyzed direct intramolecular aminotrifluoromethylation of unactivated alkenes with diverse nitrogen-based nucleophiles
Lin, Jin-Shun,Xiong, Ya-Ping,Ma, Can-Liang,Zhao, Li-Jiao,Tan, Bin,Liu, Xin-Yuan
, p. 1332 - 1340 (2014/04/03)
A mild, convenient, and step-economical intramolecular aminotrifluoromethylation of unactivated alkenes with a variety of electronically distinct, nitrogen-based nucleophiles in the presence of a simple copper salt catalyst, in the absence of extra ligand
