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Synlett
DOI: 10.1055/a-2310-0924
letter

Ni(OTf)2-catalyzed Michael Addition Reactions of 4-Hydroxycoumarins to α,β-Unsaturated 2-Acyl Imidazoles

Honghong Wang
1   School of Pharmacy, Hubei University of Science and Technology, Xianning, China (Ringgold ID: RIN418442)
,
Fan Gong
1   School of Pharmacy, Hubei University of Science and Technology, Xianning, China (Ringgold ID: RIN418442)
,
Ping Xue
2   Xianning Medical College, Hubei University of Science and Technology, Xianning, China (Ringgold ID: RIN418442)
,
Helin Lu
3   School of Pharmacy, Hubei University of Science and Technology, Xianning, China (Ringgold ID: RIN418442)
,
Xiaobo Wang
3   School of Pharmacy, Hubei University of Science and Technology, Xianning, China (Ringgold ID: RIN418442)
,
Jun Gong
4   School of Pharmacy, Hubei University of Science and Technology, Xianning, China (Ringgold ID: RIN418442)
› Author AffiliationsSupported by: National Natural Science Foundation of China 22001063
Supported by: Scientific Innovation Team of Hubei University of Science and Technology 2023T11
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An efficient Michael addition of 4-hydroxycoumarins to α,β-unsaturated 2-acyl imidazoles catalyzed by Ni(OTf)2 as a Lewis acid has been developed. A series of 4-hydroxycoumarin derivatives were obtained in excellent yields (up to 96%) with 2 mol % catalyst loading under mild conditions. Additionally, when the chiral-at-metal complex Λ-RhO was used as catalyst, moderate enantioselectivity was observed (74% ee).



Publication History

Received: 24 March 2024

Accepted after revision: 20 April 2024

Accepted Manuscript online:
20 April 2024

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