4.5 Article

Palladium-Catalyzed Sequential Cyclization/Functionalization of Oxime Ethers with Unactivated Vinyl Ethers for Tunable Assembly of Structurally Diverse Isoxazoles

期刊

CHINESE JOURNAL OF CHEMISTRY
卷 39, 期 12, 页码 3285-3291

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202100482

关键词

Palladium; Alkenes; Alkynes; Annulation; Cross-coupling

资金

  1. National Natural Science Foundation of China [21971072]
  2. Ministry of Science and Technology of the People's Republic of China [2016YFA0602900]
  3. Guangdong Natural Science Foundation [2018B030308007]
  4. Open Fund of Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates [2019B030301003]

向作者/读者索取更多资源

This study presents a novel and viable palladium-catalyzed sequential cyclization/functionalization of alkynone O-methyloximes with unactivated vinyl ethers under aerobic conditions. The structure of the products can be successfully controlled by varying the nature of the substituents of the vinyl ethers. This method offers a convenient and straightforward synthetic protocol for preparing structurally diverse compounds with promising applications in synthetic and pharmaceutical chemistry, even on a gram scale.
Main observation and conclusion A novel and viable palladium-catalyzed sequential cyclization/functionalization of alkynone O-methyloximes with unactivated vinyl ethers under aerobic conditions was described. The structure of the products could be successfully controlled by varying the nature of the substituents of the vinyl ethers. This new approach provides a convenient and straightforward synthetic protocol for the preparation of structurally diverse 4-(1-alkoxyvinyl)-isoxazoles and 4-vinylisoxazoles in moderate to good yields with highly regioselectivity. Remarkably, this protocol can be performed on a gram scale, showing the promising application in synthetic and pharmaceutical chemistry.

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