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Nickel-Catalyzed Carbonylation of Cyclopropanol with Benzyl Bromide for Multisubstituted Cyclopentenone Synthesis

Liting Hou, Wenyi Huang, Xianqing Wu, Jingping Qu and Yifeng Chen*

*School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China, Email:

L. Hou, W. Huang, X. Wu, J. Qu, Y. Chen, Org. Lett., 2022, 24, 2699-2704.

DOI: 10.1021/acs.orglett.2c00798

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A Ni-catalyzed carbonylation of cyclopropanols with benzyl bromides provides multisubstituted cyclopentenones in good yields under 1 atm of CO. The reaction proceeds through cascade carbonylation of benzyl bromides, followed by generation of nickel homoenolate from cyclopropanols via β-C elimination to afford 1,4-diketones, which undergoes intramolecular Aldol condensation.

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proposed mechanism

Key Words

Cyclopentenones, Aldol Condensation, Multicomponent Reactions

ID: J54-Y2022