Perfluoroalkyl Aziridines with Ruthenium Porphyrin Carbene Intermediates.

A new and efficient synthesis of multifunctionalized perfluoroalkyl aziridines via a ruthenium-perfluoroalkylcarbene intermediate is described. With Ru( p-Cl-TPP)CO as the catalyst, in situ generated C nF2 n+1CHN2 from C nF2 n+1CH2NH3Cl underwent a cascade of nitrone formation/1,3-diploar cycloaddition/rearrangement reactions with nitrosoarenes and alkynes to give a variety of multifunctionalized perfluoroalkyl aziridines in good to high yields and with moderate to high diastereoselectivity. The ruthenium-perfluoroalkylcarbene intermediates obtained through the stoichiometric reaction of ruthenium porphyrin and C nF2 n+1CHN2 were spectroscopically characterized.