Palladium(0)-Catalyzed Iminohalogenation of Alkenes: Synthesis of 2-Halomethyl Dihydropyrroles and Mechanistic Insights into the Alkyl Halide Bond Formation

Although the advances on carbon halide reductive elimination have been made, the alkyl bromide and chloride analogues remain a challenge. Here, a palladium(0)‐catalyzed iminohalogenation of γ,δ‐unsaturated oxime esters is described, and the use of electron‐poor phosphine ligands proved to be crucial...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-03, Vol.54 (10), p.3092-3096
Main Authors: Chen, Chen, Hou, Longlei, Cheng, Mian, Su, Jianhua, Tong, Xiaofeng
Format: Article
Language:English
Subjects:
Bromides
Carbon
Chlorides
elimination
Esters
Halides
halogenation
heterocycles
Ligands
Oximes
palladium
Phosphines
synthetic methods
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Summary:Although the advances on carbon halide reductive elimination have been made, the alkyl bromide and chloride analogues remain a challenge. Here, a palladium(0)‐catalyzed iminohalogenation of γ,δ‐unsaturated oxime esters is described, and the use of electron‐poor phosphine ligands proved to be crucial to promoting alkyl bromide and chloride reductive elimination. Furthermore, SN2‐type alkyl bromide and chloride reductive elimination has also been established. Eliminated: The use of electron‐poor phosphine ligands proved to be crucial to promoting alkyl bromide and chloride reductive elimination in the title reaction with γ,δ‐unsaturated oxime esters. Furthermore, SN2‐type alkyl bromide and chloride reductive elimination has also been established.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201410996