Nickel/Photo-Cocatalyzed Regioselective Ring Opening of N-Tosyl Styrenyl Aziridines with Aldehydes.

Abstract

Aldehydes and aziridines are both intrinsic electrophilic reagents, and thus the coupling reaction between these two compounds is highly challenging. In this protocol, the merger of nickel and hydrogen-atom-transfer photocatalysis successfully enables the ring opening of N-tosyl styrenyl aziridines with aldehydes, providing a novel and atom-economical access to a variety of β-amino ketones with complete regiocontrol. The preliminary mechanistic studies reveal that the ring opening reaction proceeds with a cooperative catalytic mode: aldehydes are converted into acyl radicals by tetrabutylammonium decatungstate under irradiation, whereas the nickel catalyst is engaged in the ring opening of aziridines and the following carbon-carbon bond-forming step.