Palladium-Catalyzed Cascade Cyclization/Alkylation of Oxime Ethers: Assembly of 4-Alkylisoxazoles by "Chain-Walking"
Yin-Long Lai1,2, Shao-Xi Yan1, Sheng-Ling Zhang1
1College of Chemistry and Civil Engineering, Shaoguan University, Shaoguan, 512005, Guangdong Province, P. R. China.
Abstract:
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.
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