Cobalt-catalyzed carbonylative formal cycloaddition of cyclopropenes and imines toward β-lactams

A cobalt-catalyzed carbonylative formal [2 + 2] cycloaddition of cyclopropenes with imines using carbon monoxide as a C1 source has been developed. • A cobalt-catalyzed carbonylative formal [2 + 2] cycloaddition of cyclopropenes with imines has been developed. • Alkenyl ketenes were generated as the key intermediates. • Various allylic β-lactams were obtained in good to excellent yields. • The reaction proceeds under mild conditions with high yields and wide substrate tolerance. We herein report a cobalt-catalyzed stereoselective carbonylative formal [2 + 2] cycloaddition of cyclopropenes with imines, providing efficient access to functionalized allylic β-lactams. The transformation proceeds through in situ generation of β-alkenyl ketene intermediates via carbon monoxide insertion into strained cyclopropenes. A broad range of substrates is tolerated, affording the corresponding β-lactams in generally good yields with high stereoselectivity under relatively mild conditions.

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Publication Details

Journal
Journal of Catalysis
Published
2026-05-12
DOI
https://doi.org/10.1016/j.jcat.2026.116951
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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article

Cobalt-catalyzed carbonylative formal cycloaddition of cyclopropenes and imines toward β-lactams

Yang Yuan, Ting Yang, Fangbei Ge, Xiao-Feng Wu
Journal of Catalysis
Cyclopropane Reaction Mechanisms
article

Cobalt-catalyzed carbonylative formal cycloaddition of cyclopropenes and imines toward β-lactams

Yang Yuan, Ting Yang, Fangbei Ge, Xiao-Feng Wu
article en

Abstract

A cobalt-catalyzed carbonylative formal [2 + 2] cycloaddition of cyclopropenes with imines using carbon monoxide as a C1 source has been developed. • A cobalt-catalyzed carbonylative formal [2 + 2] cycloaddition of cyclopropenes with imines has been developed. • Alkenyl ketenes were generated as the key intermediates. • Various allylic β-lactams were obtained in good to excellent yields. • The reaction proceeds under mild conditions with high yields and wide substrate tolerance. We herein report a cobalt-catalyzed stereoselective carbonylative formal [2 + 2] cycloaddition of cyclopropenes with imines, providing efficient access to functionalized allylic β-lactams. The transformation proceeds through in situ generation of β-alkenyl ketene intermediates via carbon monoxide insertion into strained cyclopropenes. A broad range of substrates is tolerated, affording the corresponding β-lactams in generally good yields with high stereoselectivity under relatively mild conditions.

Journal of CatalysisVol. 460
Hangzhou Normal University (CN), Dalian Institute of Chemical Physics (CN), Chinese Academy of Sciences (CN), Leibniz Institute for Catalysis (DE), Dalian National Laboratory for Clean Energy (CN)
Openalex Percentile: Top 11%
Cyclopropane Reaction Mechanisms
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