Selective cleavage and reconstruction of C–N/C–C bonds in saturated cyclic amines: tunable synthesis of lactams and functionalized acyclic amines

Abstract

Selective cleavage and functionalization of C–N/C–C bonds in saturated cyclic amines under the promotion of oxoammonium salt and tert-butyl hydroperoxide in the presence of different additives have been developed. To be specific, cascade cleavage and reconstruction of C–N and C–C bonds took place under acidic conditions to provide pyrrolidin-2-ones. Under basic conditions, on the other hand, selective cleavage and functionalization of C–C bonds occurred to afford multi-functionalized acyclic N-formal amines. In addition, studies for revealing the intriguing reaction mechanisms have also been performed.