1401714-03-1Relevant articles and documents
Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay
Fu, Liang,Zhou, Song,Wan, Xiaolong,Chen, Pinhong,Liu, Guosheng
, p. 10965 - 10969 (2018)
A novel enantioselective copper-catalyzed trifluoromethylalkynylation of styrenes, proceeding through a radical relay process, is described herein, which affords structurally diverse CF3-containing propargylic compounds in good yield with excellent enantioselectivities under very mild conditions. In addition, the reaction features wide substrate scope and good functional group tolerance. Moreover, the trifluoromethylalkynylated products can be easily converted into synthetically useful chiral terminal alkynes, allenes, Z-alkenes, as well as CF3-modified nonsteroidal anti-inflammatory drugs.
Determination of rate constants for trifluoromethyl radical addition to various alkenes via a practical method
Hartmann,Li,Studer
, p. 206 - 210 (2015/12/30)
A simple and practical method for the determination of rate constants for trifluoromethyl radical addition to various alkenes by applying competition kinetics is introduced. In the kinetic experiments the trifluoromethyl radicals are generated in situ from a commercially available hypervalent-iodine-CF3 reagent (Togni-reagent) by SET-reduction with TEMPONa in the presence of TEMPO and a π-acceptor. From the relative ratio of TEMPOCF3 and CF3-addition product formed, which is readily determined by 19F-NMR spectroscopy, rate constants for trifluoromethyl radical addition to the π-acceptor can be calculated. The practical method is also applicable to measure rate constants for the addition of other perfluoroalkyl radicals to alkenes as documented for CF3CF2-radical addition reactions.
Copper-Catalyzed Intermolecular Trifluoromethylthiocyanation of Alkenes: Convenient Access to CF3-Containing Alkyl Thiocyanates
Liang, Zhaoli,Wang, Fei,Chen, Pinhong,Liu, Guosheng
supporting information, p. 2438 - 2441 (2015/05/27)
A highly selective and efficient approach for the direct trifluoromethylthiocyanation of alkenes has been developed using trimethylsilyl isothiocyanate (TMSNCS) as the thiocyanating agent and Togni reagent as the CF3 source in the presence of copper(I) catalyst. Both activated and unactivated alkenes work well to deliver various CF3-containing thiocyanates.
Copper-catalyzed intermolecular trifluoromethylarylation of alkenes: Mutual activation of arylboronic acid and CF3+ reagent
Wang, Fei,Wang, Dinghai,Mu, Xin,Chen, Pinhong,Liu, Guosheng
supporting information, p. 10202 - 10205 (2014/08/05)
A novel copper-catalyzed intermolecular trifluoromethylarylation of alkenes is developed using less active ether-type Togni's reagent under mild reaction conditions. Various alkenes and diverse arylboronic acids are compatible with these conditions. Preliminary mechanistic studies reveal that a mutual activation process between arylboronic acid and CF3+ reagent is essential. In addition, the reaction might involve a rate-determining transmetalation, and the final aryl C-C bond is derived from reductive elimination of the aryl(alkyl)Cu(III) intermediate.
Transition-metal-free trifluoromethylaminoxylation of alkenes
Li, Yi,Studer, Armido
supporting information; experimental part, p. 8221 - 8224 (2012/09/07)
No transition metal! Fluorinated hypervalent-iodine reagents react with TEMPONa in the presence of an alkene under mild conditions to give the corresponding perfluoroalkylaminoxylation products. These radical addition/trapping reactions occur with high st
