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

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Abstract

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.

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

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Publication details

The article was received on 22 Jul 2019, accepted on 08 Aug 2019 and first published on 14 Aug 2019


Article type: Communication
DOI: 10.1039/C9CC05668H
Chem. Commun., 2019, Advance Article

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

    P. Shi, J. Wang, Z. Gan, J. Zhang, R. Zeng and Y. Zhao, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC05668H

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