Photocatalytic amidation and esterification with perfluoroalkyl iodide

Effect of excited-state properties and mechanistic study on visible-light induced photocatalytic amidation and esterification with perfluoroalkyl halides under mild conditions.

Stereoselective synthesis of fluoroalkylated (Z)-alkene via nickel-catalyzed and iron-mediated hydrofluoroalkylation of alkynes

An efficient nickel-catalyzed, iron-mediated hydrofluoroalkylation of alkynes with bromodifluoroacetate or perfluoroalkyl iodide, which proceeded smoothly to give fluoroalkylated (Z)-alkenes with high stereocontrol (up to 99 : 1 Z/E), was developed.

Visible-light mediated cascade cyclization of ene-vinylidenecyclopropanes: access to fluorinated heterocyclic compounds

A fluoroalkylation and cycloisomerization cascade reaction of ene-VDCP with ethyl iododifluoroacetate or perfluoroalkyl iodide upon visible-light irradiation was disclosed in this paper, affording the desired fluorinated cyclization products in moderate...

Synthesis of Perfluoroalkyl-Substituted Oxindoles through Organophotoredox-Catalyzed Perfluoroalkylation of N-arylacrylamides with Perfluoroalkyl Iodides

An efficient process was developed for the perfluoroalkylation of N-arylacrylamides through an organocatalyzed photoredox/cyclization reaction of N-arylacrylamides with inexpensive perfluoroalkyl iodide reagents. The reaction employs an inexpensive organic dye, eosin Y, as the photoredox catalyst and is run under irradiation by a 26 W LED lightbulb.

Aza-tricycles containing a perfluoroalkyl group: synthesis, structure and fluorescence

Perfluoroalkyl-containing aza-tricycles have been prepared in one synthetic operation via an ambient light-promoted three-component reaction of β-oxo esters, perfluoroalkyl iodide and DBU.

Study of the Halogen Bonding between Pyridine and Perfluoroalkyl Iodide in Solution Phase Using the Combination of FTIR and 19F NMR

Halogen bonding between pyridine and heptafluoro-2-iodopropane (iso-C3F7I)/heptafluoro-1-iodopropane (1-C3F7I) was studied using a combination of FTIR and 19F NMR. The ring breathing vibration of pyridine underwent a blue shift upon the formation of halogen bonds with both iso-C3F7I and 1-C3F7I. The magnitudes of the shifts and the equilibrium constants for the halogen-bonded complex formation were found to depend not only on the structure of the halocarbon, but also on the solvent. The halogen bond also affected the Cα-F (C-F bond on the center carbon) bending and stretching vibrations in iso-C3F7I. These spectroscopic effects show some solvent dependence, but more importantly, they suggest the possibility of intermolecular halogen bonding among iso-C3F7I molecules. The systems were also examined by 19F NMR in various solvents (cyclohexane, hexane, chloroform, acetone, and acetonitrile). NMR dilution experiments support the existence of the intermolecular self-halogen bonding in both iso-C3F7I and 1-C3F7I. The binding constants for the pyridine/perfluoroalkyl iodide halogen bonding complexes formed in various solvents were obtained through NMR titration experiments. Quantum chemical calculations were used to support the FTIR and 19F NMR observations.