[3+2] Cross Coupling of Aziridines with Isocyanates Catalyzed by Nickel

Abstract

Cycloaddition of aziridines with phenyl isocyanate proceeded smoothly in the presence of nickel catalysts and five-membered heterocycles were isolated in good yields. The best result was obtained when the reaction was carried out in the presence of NiI₂. The selective formation of iminooxazolidine derivatives was observed in the reaction of N-benzylaziridine with phenyl isocyanate. On the other hand, the reaction of N-tosylaziridine with phenyl isocyanate proceeded smoothly in the presence of Ni(PPh₃)₂I₂ and an imidazolidinone derivative was isolated. The mechanism of the reaction was also proposed.

Scheme 1