Copper-catalyzed iminohalogenation of γ, δ-unsaturated oxime esters with halide salts: Synthesis of 2-halomethyl pyrrolines

[Display omitted] •First copper-catalyzed iminohalogenation of γ, δ-unsaturated oxime esters with KX (X = I, Br, Cl).•Readily available catalyst and halide source.•New method for the efficient synthesis of diversiform 2-halomethyl pyrrolines.•Good functional group compatibility, moderate to excellen...

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Veröffentlicht in:Tetrahedron letters 2019-09, Vol.60 (36), p.151000, Article 151000
Hauptverfasser: Chen, Chen, Ding, Jie, Wang, Yuebo, Shi, Xiaonan, Jiao, Dequan, Zhu, Bolin
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Sprache:eng
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Zusammenfassung:[Display omitted] •First copper-catalyzed iminohalogenation of γ, δ-unsaturated oxime esters with KX (X = I, Br, Cl).•Readily available catalyst and halide source.•New method for the efficient synthesis of diversiform 2-halomethyl pyrrolines.•Good functional group compatibility, moderate to excellent yields, simple operations. A copper-catalyzed iminohalogenation of unactivated alkenes of γ, δ-unsaturated oxime esters is achieved by using readily available halide salts. Utilizing this protocol, a sequence of structurally diversiform 2-halomethyl pyrrolines are efficiently synthesized and a mechanism involving iminyl radical intermediates, which were initiated by Cu(I) species, was proposed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151000