Use of 1,3-dipolar reactions for the preparation of SF5-substituted five-membered ring heterocycles. Pyrroles and thiophenes

In situ-generated unsubstituted, “parent” azomethine and thiocarbonyl ylides are used to prepare a large variety of 3-aryl- and alkyl-substituted, 4-pentafluorosulfanylpyrroles and 3-aryl-substituted, 4-pentafluorosulfanylthiophenes, the latter of which are to our knowledge the first reported SF₅-substituted thiophenes. The 1,3-cycloadditions of these ylides with aryl and alkyl, SF₅-alkynes produce dihydro-pyrroles and thiophenes, which without isolation can then be oxidatively aromatized to the respective pentafluorosulfanylpyrroles and thiophenes in good yield.