Synthesis of Unprotected β-Arylethylamines by Iron(II)-Catalyzed 1,2-Aminoarylation of Alkenes in Hexafluoroisopropanol.

β-Arylethylamines are prevalent structural motifs in molecules exhibiting biological activity. Here we report a sequential one-pot protocol for the 1,2-aminoarylation of alkenes with hydroxylammonium triflate salts and (hetero)arenes. Unlike existing methods, this reaction provides a direct entry to unprotected β-arylethylamines with remarkable functional group tolerance, allowing key drug-oriented functional groups to be installed in a two-step process.

Halogen bonding effect on electrochemical anion oxidation in ionic liquids.

Three Ionic liquids (ILs) based on an imidazolium core have been compared and used as solvents for the oxidation of various anions. Electrochemical experiments as well as NMR titrations and X-ray diffraction analyses unambiguously confirm the crucial role of non-covalent halogen bonding on the oxidation potentials and consequently the electrochemical window of the respective ILs.

Towards redox-switchable organocatalysts based on bidentate halogen bond donors.

Redox-active bidentate halogen bond donors based on halopyridinium groups as halogen-bond donating units were synthesized and their structures were elucidated by X-ray diffraction analyses and DFT calculations. Via reversible twofold reduction, these dicationic species can be transformed to neutral compounds which should be much weaker Lewis acids. The corresponding electrochemical data were obtained, and CV as well as UV-vis and NMR techniques were also used to determine binding constants of these halogen bond donors to halides.

Modulating alkene reactivity from oxygenation to halogenation electrochemical O activation by Mn porphyrin.

Oxidation of organic substrates is achieved in nature under mild conditions thanks to metalloenzymes but remains a challenge for chemists. Herein we show by UV-Vis spectroelectrochemistry that when MnIIITPPCl is electrochemically reduced to MnII in CH2Cl2 under O2, a MnIIO2˙ species is generated. Benzoic anhydride reacts with the latter triggering a catalytic current in cyclic voltammetry.

Electrocatalytic O Activation by Fe Tetrakis(pentafluorophenyl)porphyrin in Acidic Organic Media. Evidence of High-Valent Fe Oxo Species.

O activation under mild conditions remains a weighty challenge for chemists. Herein we report a study of electrochemical O reductive activation catalyzed by Fe(FTPP)Cl, by means of cyclic voltammetry and UV-vis spectroelectrochemistry in acidic solutions of ,-dimethylformamide. Two parallel catalytic pathways have been evidenced occurring at different overpotentials.