Synthesis of gem‐Difluorinated Isoxazoles via Palladium‐Catalyzed Oxylallylation of Alkynone Oxime Ethers

A novel and reliable palladium‐catalyzed oxylallylation of alkynone oxime ethers with fluorine‐containing alkenes was accomplished. Using the bulk industrial chemical 3‐bromo‐3,3‐difluoroprop‐1‐ene as the coupling partner, this synthetic methodology offers the first example for the assembly of struc...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2023-09, Vol.18 (18), p.e202300579-n/a
Main Authors: Li, Jianxiao, Hong, Chenjing, Niu, Yanan, Wang, Bowen, Xiong, Wenfang, Jiang, Huanfeng
Format: Article
Language:English
Subjects:
alkenes• alkynes
cascade reaction
Chemistry
Ethers
Fluorine
Functional groups
isoxazoles
Palladium
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Summary:A novel and reliable palladium‐catalyzed oxylallylation of alkynone oxime ethers with fluorine‐containing alkenes was accomplished. Using the bulk industrial chemical 3‐bromo‐3,3‐difluoroprop‐1‐ene as the coupling partner, this synthetic methodology offers the first example for the assembly of structurally diverse gem‐difluorinated isoxazole derivatives in moderate to good yields with high atom‐ and step‐economy and excellent functional group compatibility. More importantly, this strategy allows for the direct combination of the isoxazole motifs and gem‐difluoroalkene unit, which is not easy to obtain through a general synthetic strategy. An efficient palladium‐catalyzed oxylallylation of alkynone oxime ethers with fluorine‐containing alkenes for the assembly of structurally diverse gem‐difluorinated isoxazole derivatives is described. This approach features high atom‐ and step‐economies, excellent functional groups compatibilities, and diverse transformations.
ISSN:1861-4728
1861-471X
1861-471X
DOI:10.1002/asia.202300579