Preparation and evaluation of nitrene precursors (PhI=NSO2Ar) for the copper-catalyzed aziridination of olefins

✍ Scribed by Mikael J. Södergren; Diego A. Alonso; Ashutosh V. Bedekar; Pher G. Andersson

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 212 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01589-x

✦ Synopsis

The preparation of different lN-(arenesulfonyl)iminolphenyliodinanes is described along with an evaluation of their utility as nitrene precursors for the copper-catalyzed aziridination of different olefins. The best results were obtained with p-NO2-Cr, H, flO~=IPh and p-MeO-Ce~I4SO2N=IPh, both of which were found superior to Phl=NTs, which previously has been the reagent of choice for this type of reaction. The corresponding aziridine derivatives were obtained in good to excellent yields (60-99%) using 1.0 equivalent of olefin and 1.5 equivalents of the nitrene precursor.