Combining visible-light induction and copper catalysis for chemo-selective nitrene transfer for late-stage amination of natural products.
Commun Chem
; 5(1): 79, 2022 Jul 06.
Article
en En
| MEDLINE
| ID: mdl-36697627
ABSTRACT
Nitrene transfer chemistry is an effective strategy for introducing C-N bonds, which are ubiquitous in pharmaceuticals, agrochemicals and diverse bioactive natural products. The development of chemical methodology that can functionalize unique sites within natural products through nitrene transfer remains a challenge in the field. Herein, we developed copper catalyzed chemoselective allylic C-H amination and catalyst-free visible-light induced aziridination of alkenes through nitrene transfer. In general, both reactions tolerate a wide range of functional groups and occur with predictable regioselectivity. Furthermore, combination of these two methods enable the intermolecular chemo-selective late-stage amination of biologically active natural products, leading to C-H amination or C=C aziridination products in a tunable way. A series of control experiments indicate two-step radical processes were involved in both reaction systems.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Commun Chem
Año:
2022
Tipo del documento:
Article
País de afiliación:
China