A radical addition reaction of Py-SF4Cl to alkynes and alkenes provide pyridine-SF4-alkenes and pyridine-SF4-alkanes under blue LED light irradiation or absence of light irradiation in CPME or without solvent.
We report a new protocol to form pentafluorosulfanyl (hetero)arenes via chlorine-fluorine exchange of (hetero)aryl tetrafluorosulfanyl chlorides by AgBF4. The method enables access to electron-deficient pentafluorosulfanyl(hetero)arenes, which are targets that are difficult to synthesize. Two advantages of AgBF4 are its ease of handling and stability. This would be a general transformation protocol.
Herein, we report the metal-free hydration of pyridine-SF 4 -alkynes, under acidic conditions and with reaction durations ranging from 5 min to 10 h at room temperature, to synthesize pyridine-SF 4 -methyl ketones in yields of 59−93%. Further, we demonstrate the synthetic applications of the synthesized pyridine-SF 4 -methyl ketones, such as chlorination, NaBH 4 reduction, Baeyer− Villiger oxidation, and the generation of enol-triflates. These compounds hold promise as useful building blocks in the syntheses of a wide range of SF 4 -containing drug candidates.
Alkyne hydroamination is an effective approach for the production of enamines and enamine‐containing N‐heterocycles. However, stereoselectivity control is a considerable challenge in this reaction because of the electronic repulsion between an incoming nitrogen lone pair and the alkyne π‐system. Herein, we propose a methodology involving β‐regio‐ and Z‐selective alkyne hydroamination by using tetrafluoro‐λ6‐sulfanyl (SF4) alkynes under superbasic, naked anion conditions. The reaction is compatible with a wide variety of N‐heterocycles, including indoles, carbazoles, pyrazoles, and imidazoles, and selectively furnishes SF4‐linked Z‐vinyl enamines with β‐regioselectively. Moreover, the method can be extended to the β‐ and Z‐controlled, base‐mediated alkyne hydrophenoxylation with phenols to provide SF4‐linked Z‐vinyl ethers in high yields. As the SF4 unit has attracted attention as a bioisostere for alkynes, p‐benzenes, bicyclo[1.1.1]pentyl (BCP) groups, and cubanes in medicinal chemistry, this chemistry represents an effective approach to creating novel drug candidates incorporating SF4‐containing molecules.
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