Issue 18, 2021

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
01 May 2021
Accepted
13 Jul 2021
First published
15 Jul 2021

Org. Chem. Front., 2021,8, 5118-5123

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

Y. He, J. Yang, X. Zhang and X. Fan, Org. Chem. Front., 2021, 8, 5118 DOI: 10.1039/D1QO00689D

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