Palladium‐Catalyzed Cascade Cyclization/Alkylation of Oxime Ethers: Assembly of 4‐Alkylisoxazoles by “Chain‐Walking” Strategy

A reliable and efficient palladium‐catalyzed cascade cyclization/alkylation of oxime ethers with unactivated alkenes is described, affording a whole variety of structurally diverse isoxazole derivatives in moderate to good yields with excellent functional group compatibility. Ionic liquid [Aeim]Br n...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2022-11, Vol.17 (21), p.e202200806-n/a
Main Authors: Lai, Yin‐Long, Yan, Shao‐Xi, Zhang, Sheng‐Ling, Huang, Yu‐Hong, Hu, Ru‐Xin, Chen, Yang‐Chong, Luo, Jian‐Min, Li, Jianxiao
Format: Article
Language:English
Subjects:
4-alkylisoxazoles
Accelerating agents
alkenes
Alkylation
alkynes
Bromine
Chains
Chemical synthesis
Chemistry
Ethers
Functional groups
Ionic liquids
Methyl bromide
Palladium
palladium-catalyzed
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Summary:A reliable and efficient palladium‐catalyzed cascade cyclization/alkylation of oxime ethers with unactivated alkenes is described, affording a whole variety of structurally diverse isoxazole derivatives in moderate to good yields with excellent functional group compatibility. Ionic liquid [Aeim]Br not only acts as an environmentally friendly solvent but also acts as an accelerating agent to provide excess bromine source to eliminate bromomethane from oxime ethers. More importantly, the use of “chain‐walking” strategy provides a novel methodology in organic synthesis to rapid generation of molecular complexity from readily available starting materials. “Chain‐Walking” alkylation: A reliable and efficient palladium‐catalyzed cascade cyclization/alkylation of oxime ethers with unactivated alkenes is described, affording a whole variety of structurally diverse isoxazole derivatives in moderate to good yields with excellent functional group compatibility.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.202200806