1335135-19-7Relevant articles and documents
Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process
Wang, Fei,Wang, Dinghai,Wan, Xiaolong,Wu, Lianqian,Chen, Pinhong,Liu, Guosheng
, p. 15547 - 15550 (2016)
A novel enantioselective copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes has been developed, in which a variety of CF3-containing alkylnitriles are furnished with excellent enantiomeric excess. Preliminary mechanistic studies revealed (1) the reaction was initiated by a SET process between activated Togni's CF3+ reagent and a Cu(I) catalyst; (2) the released CF3 radical readily added to styrene to provide a benzylic radical, which was then trapped by a chiral Cu(II) cyanide species to deliver the desired alkylnitriles; (3) a low concentration of the CN anion was crucial to obtain high enantioselectivity.
Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination
Sun, Jiyun,Zhen, Xiaohua,Ge, Huaibin,Zhang, Guangtao,An, Xuechan,Du, Yunfei
, p. 1452 - 1458 (2018)
The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.
Copper(I)-Catalyzed Intramolecular Trifluoromethylation of Methylenecyclopropanes
Zhu, Zi-Zhong,Chen, Kai,Yu, Liu-Zhu,Tang, Xiang-Ying,Shi, Min
, p. 5994 - 5997 (2015)
Copper(I)-catalyzed intramolecular trifluoromethylation of methylenecyclopropanes has been developed to produce a variety of CF3-substituted dihydronaphthalenes in moderate to good yields, relying on the construction of C(sp2)-CFsub
Carbon-Carbon Bond-Forming Reductive Elimination from Isolated Nickel(III) Complexes
Bour, James R.,Camasso, Nicole M.,Meucci, Elizabeth A.,Kampf, Jeff W.,Canty, Allan J.,Sanford, Melanie S.
, p. 16105 - 16111 (2016)
This manuscript describes the design, synthesis, characterization, and reactivity studies of organometallic NiIII complexes of general structure TpNiIII(R)(R1) (Tp = tris(pyrazolyl)borate). With appropriate selection of th
A Readily Available Trifluoromethylation Reagent and Its Difunctionalization of Alkenes
Zhang, Min,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information, p. 6079 - 6083 (2021/08/16)
Trifluoromethyl substitution is notably popular in pharmaceuticals and agrochemicals; however, trifluoromethylated compounds normally rely on the use of cost-prohibitive or gaseous trifluoromethylating reagents, which diminishes the general applicability of these methods. Herein an efficient trifluoromethylation reagent trifluoromethylsulfonyl-pyridinium salt (TFSP) was reported, which can be readily prepared from cheap and easily available bulk industrial feedstocks. TFSP can generate a trifluoromethyl radical under photocatalysis and realize the effective azido- or cyano-trifluoromethylation reactions of alkenes.
Metal-Free Visible-Light-Promoted Trifluoromethylation of Vinylcyclopropanes Using Pyrylium Salt as a Photoredox Catalyst
Chandu, Palasetty,Ghosh, Krishna Gopal,Sureshkumar, Devarajulu
, p. 8771 - 8781 (2019/08/30)
Visible-light-induced metal-free trifluoromethylation of activated, carbocyclic, and unactivated vinylcyclopropanes via a ring-opening reaction using the Langlois reagent (CF3SO2Na) is reported to synthesize allylic trifluoromethylated derivatives. Allylic trifluoromethylation was achieved by a photo-oxidative single electron transfer (SET) process at an ambient temperature and under metal-free conditions and visible-light irradiation using pyrylium salt as a photoredox catalyst. The reported methodology has an operational simplicity, broad substrate scope, high functional group tolerance, and scalability.
