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: yifengchen
ecust.edu.cn
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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Abstract
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
