No abstract

Pyridine-trans-SF4-alkenes or -alkanes have been synthesized for the first time via the radical addition reactions of pyridine-trans-SF4Cl to alkynes or alkenes in good to high yields.

Electrophilic pentafluorosulfanyl (SF) heteroarylation of target molecules using novel reagents is described. Unsymmetrical diaryliodonium reagents 1 having 2-SF-pyridine have been synthesized in good yields. They are efficient electrophilic reagents for carbon and heterocentered nucleophiles, producing the corresponding SF-pyridine derivatives in good to excellent yields.

An eccentric trans-SF4 unit achieves a rod-like linear connection of two independent N-heterocycles, pyridines and triazoles.

Conscious of the potential bioactivity of fluorine, an investigation was conducted using various fluorine-containing diaryliodonium salts in order to study and compare their biological activity against human lymphoma U937 cells. Most of the compounds tested are well-known reagents for fluoro-functionalized arylation reactions in synthetic organic chemistry, but their biological properties are not fully understood. Herein, after initially investigating 18 fluoro-functionalized reagents, we discovered that the ortho-fluoro-functionalized diaryliodonium salt reagents showed remarkable cytotoxicity in vitro. These results led us to synthesize more compounds, previously unknown sterically demanding diaryliodonium salts having a pentafluorosulfanyl (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ6-sulfanyl)phenyl)iodonium exhibited the greatest potency in vitro against U937 cells. Evaluation of the cytotoxicity of selected phenylaryl-λ3-iodonium salts against AGLCL (a normal human B cell line) was also examined.