A practical copper-catalyzed approach to β-lactams via radical carboamination of alkenyl carbonyl compounds

Functionalized β-lactams are highly important motifs in synthetic chemistry. We report an efficient and novel approach to the synthesis of β-lactams via a copper(i)-catalyzed cascade process involving C(benzyl)-H radical abstraction, intermolecular alkene addition, and intramolecular amination react...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-08, Vol.55 (71), p.10523-10526
Main Authors: Shi, Peng, Wang, Jie, Gan, Zixu, Zhang, Jingyu, Zeng, Runsheng, Zhao, Yingsheng
Format: Article
Language:English
Subjects:
Alkenes
Carbonyl compounds
Carbonyls
Catalysis
Copper
Copper compounds
Crystallography
Free radicals
Organic chemistry
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Summary:Functionalized β-lactams are highly important motifs in synthetic chemistry. We report an efficient and novel approach to the synthesis of β-lactams via a copper(i)-catalyzed cascade process involving C(benzyl)-H radical abstraction, intermolecular alkene addition, and intramolecular amination reaction. Variously substituted alkenes were synthesized from vinylacetic acid, leading to the corresponding β-lactams in moderate to good yields. Preliminary studies indicate that the reaction undergoes a free radical mechanism via a Cu(i)/Cu(ii)/Cu(iii) catalytic cycle.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc05668h