A variety of β-azidotetraarylporphyrins were conveniently synthesized by classical conversion of the amino groups of β-aminotetraarylporphyrins into azido groups through diazotization and subsequent treatment with sodium azide. Their thermal reaction and Cu^I-catalyzed 1,3-dipolar cycloaddition with various alkynes were also reported. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

A series of 10,20-diaryl-5-[(E)-fluoroalkenyl]-15-(fluoroalkyl)porphyrins has been synthesized by the reaction of free-base 5,15-diarylporphyrins with fluoroalkyl iodides in the presence of Na₂S₂O₄. Subsequent intramolecular cyclization of the corresponding (fluoroalkenyl)porphyrins occurs smoothly in refluxing toluene/H₂O. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Difluoro(methylene)cyclopropanes (F₂MCPs) were prepared directly by difluorocarbene addition to allenes, and the resulting F₂MCPs were converted into a variety of difluoro(methylene)cyclopropane derivatives through Heck reactions and electrophilic substitutions. The ring-opening reactions of F₂MCPs with I₂ are reported and a plausible reaction mechanism is also discussed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

A simple and facile fluorous biphasic catalytic oxidation of alkenes and aldehydes with 1 atm of air and 2-methylpropanal in the presence of the (β-perfluoroalkylated tetraphenylporphyrin)cobalt complexes [Co{TPP(C₈F₁₇)₄}] (Co2) has been demonstrated for the first time. This kind of β-perfluoroalkylated tetraphenylporphyrin may be used in other catalytic applications because of its ready availability and unique properties. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

The cycloaddition reactions of α-acetyoxyl propynes with difluorocarbene, generated from the decomposition of FSO₂CF₂CO₂SiMe₃ in DG in the presence of 10% of NaF at 120 °C gave readily α-acetyoxyl gem-difluorocyclopropenes. When these fluorinated compounds were hydrolyzed under alkaline condition at 0 °C, α-hydroxyl cyclopropenones were produced predominantly whereas treated with catalytic amounts of BF₃·Et₂O in Et₂O, α-acetyoxyl cyclopropenones were obtained.

We report three crystal structures of a synthetic 5-fluoroalkylporphyrin molecule that was programmed for self-assembly. All the X-ray structures of zincated and free-base porphyrins Zn2 b, Zn5 a, and 2 b revealed rigorous π–π stacking and extremely hydrophobic interactions. Other the other hand, the strong aggregation of 5-fluoroalkylporphyrins in solution was also found. Interestingly, the regular nanopore formation of the 5-fluoroalkylporphyrin was visualized by atomic force microscopy (AFM). Importantly, the 5-fluoroalkylporphyrins possess liquid-crystalline properties that were confirmed by using a combination of differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) techniques. By comparison, the self-assembly of non-fluorine-containing porphyrins with similar structure showed much lower aggregation ability, as investigated by NMR techniques. Additionally, no birefringent mesophase was observed for the non-fluorine-containing porphyrin.

2-Fluoro-1-phenyl-1-trimethylsiloxyethene reacted efficiently with aldehydes to give α-fluoro β-hydroxy ke-tones in HMPA in the presence of Zn powder and CuCl.

Heating a mixture of 1, 3-diiodo-1, 1,3, 3-tetrafluoropropane (2), K₂CO₃, pyridinium bromides (3) in CH₃CN at 65°C for 10 h gives the corresponding trifluoromethylindolizines.

Treatment of difluorodiiodomethane with TV-sodium salts of imidazoles at - 15 °C gave N-difluoroiodomethylated imidazoles (3) in good yields. The addition of 3 to alkyne or alkenes initiated by sodium dithionate at room temperature resulted in the corresponding adducts in high yields.