Unexpected copper-catalyzed aminohalogenation reaction of olefins using N-halo-N-metallo-sulfonamide as the nitrogen and halogen sources

N-Chloro-N-sodium-sulfonamide was found to react with olefins in the presen ce of copper catalyst to give vicinal haloamine derivatives instead of azir idines. The resulting regio and stereochemistry indicates that this unexpec ted reaction could proceed through the formation of unprecedented N-chloro- M-copper-2-nitrobenzenesulfonyl aziridinium intermediates, which can increa se the successful chance to render the asymmetric version of the aminohalog enation reaction. In addition, this finding provides a more convenient prot ocol by the use of solely pure NsNClNa for the aminohalogenation reaction a s compared to the mixed nitrogen and chlorine sources consisting of NSNCl2 and NsNHNa as previously reported by us. Two new simple olefin substrates, trans-stilbene and styrene, were also found to be effective for this new re action system. (C) 2001 Elsevier Science Ltd. All rights reserved.