Combining visible-light induction and copper catalysis for chemo-selective nitrene transfer for late-stage amination of natural products

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 r...

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Bibliographic Details
Published in:Communications chemistry 2022-07, Vol.5 (1), p.79-9, Article 79
Main Authors: Xing, Qi, Jiang, Ding, Zhang, Jiayin, Guan, Liangyu, Li, Ting, Zhao, Yi, Di, Man, Chen, Huangcan, Che, Chao, Zhu, Zhendong
Format: Article
Language:English
Subjects:
639/638/403/933
639/638/77/888
Agrochemicals
Alkenes
Catalysis
Catalysts
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Copper
Functional groups
Natural products
Regioselectivity
System effectiveness
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Summary: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. Nitrene transfer chemistry is an effective strategy for introducing C–N bonds, but inexpensive reaction systems for tunable, intermolecular chemoselective nitrene transfer for late-stage amination of unsaturated natural products remains a challenge. Here, the authors report copper catalysed chemoselective allylic C–H amination and catalyst-free visible-light induced aziridination of alkenes through nitrene transfer.
ISSN:2399-3669
2399-3669
DOI:10.1038/s42004-022-00692-6