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 |
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Format: | Artikel |
Sprache: | eng |
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•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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2019.151000 |