Rhodium(II)-catalyzed aziridinations and CH insertions with [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane

Abstract

The [Rh2(OAc)4]-catalyzed decomposition of NsN(DOUBLE BOND)IPh {[N-(p-nitrobenzenesulfonyl)imino]phenyliodinane} in the presence of olefins affords aziridines in yields of up to 85%. The aziridination of cis-hex-2-ene and cis-β-methylstyrene is stereospecific, but, cis-stilbene affords a 3:1 mixture of cis- and trans-aziridines in low yield. With chiral Rh(II) catalysts, optically active aziridines are formed having enantiomeric excesses of up to 73%. The NsN(DOUBLE BOND)IPh-[Rh2(OAc)4] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents.