83015-33-2Relevant articles and documents
Selective fluoroalkylation of thiophenols by 1,2-dibromotetrafluoroethane activated by sulfur dioxide
Koshechko, Vyacheslav G.,Kiprianova, Lydiya A.,Fileleeva, Ludmyla I.,Kalinina, Ludmyla I.
, p. 1376 - 1378 (2007)
Treatment of 1,2-dibromotetrafluoroethane with thiophenols in DMF in the presence of sulfur dioxide and pyridines having pKa > 5 gives fluoroalkylated thioethers in high yields under mild conditions. The influence of thiophenol reactant structu
Expanding the Scope of Hypervalent Iodine Reagents for Perfluoroalkylation: From Trifluoromethyl to Functionalized Perfluoroethyl
Matouek, Vclav,Vclavk, Ji,Hjek, Peter,Charpentier, Julie,Blastik, Zsfia E.,Pietrasiak, Ewa,Budinsk, Alena,Togni, Antonio,Beier, Petr
, p. 417 - 424 (2016/01/25)
A series of new hypervalent iodine reagents based on the 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole and 1,2-benziodoxol-3-(1H)-one scaffolds, which contain a functionalized tetrafluoroethyl group, have been prepared, characterized, and used in synthetic applications. Their corresponding electrophilic fluoroalkylation reactions with various sulfur, oxygen, phosphorus, and carbon-centered nucleophiles afford products that feature a tetrafluoroethylene unit, which connects two functional moieties. A related λ3-iodane that contains a fluorophore was shown to react with a cysteine derivative under mild conditions to give a thiol-tagged product that is stable in the presence of excess thiol. Therefore, these new reagents show a significant potential for applications in chemical biology as tools for fast, irreversible, and selective thiol bioconjugation.
Copper(0)-mediated fluoroalkylation of iodobenzene with 2-bromo-1,1,2,2-tetrafluoroethyl compounds: Investigation on the influence of R substituent on the reactivity of RCF2Cu species
Zhu, Jieming,Ni, Chuanfa,Gao, Bing,Hu, Jinbo
, p. 139 - 147 (2015/03/04)
We have made a systematic investigation on the copper(0)-mediated tetrafluoroethylenation of iodobenzene with structurally diverse 2-bromo-1,1,2,2-tetrafluoroethyl compounds. A comparison of this reaction with 1,2,2-trifluoro-1-phenylethylation and the known functionalized difluoroalkylation demonstrates that the substituent R of α,α-difluoroalkyl copper species RCF2Cu plays a crucial role on their reactivity, which is believed to be useful for the development of new fluoroalkylation reactions under the promotion of transition metals.