Palladium(II) mediated aziridination of olefins with bromamine-T as the nitrogen source: scope and mechanism

The palladium(II)-promoted reaction of a variety of olefins and bromamine-T provided N-tosyl-2-substituted aziridines under mild conditions. Olefins bearing chiral appendages gave only a poor to modest diastereoselectivity. Appropriate deuterated olefins were selected to study the stereochemistry of the reaction. A Pd(IV) intermediate is proposed as the aziridinating species.

A simple method is described for the palladium(II) mediated aziridination of a broad range of olefins using bromamine-T as the nitrogen source.