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Cu(OTf)2-Phosphoric Acid-Catalyzed Tandem Oxa-Nazarov Cyclization and Dibromination of Conjugated 1,2-Diketones

Hongchao Yin, Yuan Tian, Chenxi Guo, Ran Song, Daoshan Yang, Jian Lv*

*College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao 266042, China, Email: lvjianiccas.ac.cn

H. Yin, Y. Tian, C. Guo, R. Song, D. Yang, J. Lv, J. Org. Chem., 2023, 88, 15862-15870.

DOI: 10.1021/acs.joc.3c01941


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Abstract

The combination of Cu(OTf)2 and diphenyl phosphate (DPP-H) catalyzes a facile tandem oxa-Nazarov cyclization and dibromination of conjugated 1,2-diketones and N-bromosuccinimide to provide 2,4-dibromo-3(2H)-furanones in good yields.

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proposed mechanism

Key Words

3(2H)-furanones, Nazarov cyclization, NBS

ID: J42-Y2023