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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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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cited_by cdi_FETCH-LOGICAL-c6216-6203fb9b5048263c059aafa62686824f4e0e0132222f2c34e9beabbdcd4646de3
cites cdi_FETCH-LOGICAL-c6216-6203fb9b5048263c059aafa62686824f4e0e0132222f2c34e9beabbdcd4646de3
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container_issue 10
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container_title Angewandte Chemie International Edition
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creator Chen, Chen
Hou, Longlei
Cheng, Mian
Su, Jianhua
Tong, Xiaofeng
description 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.
doi_str_mv 10.1002/anie.201410996
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subjects Bromides
Carbon
Chlorides
elimination
Esters
Halides
halogenation
heterocycles
Ligands
Oximes
palladium
Phosphines
synthetic methods
title Palladium(0)-Catalyzed Iminohalogenation of Alkenes: Synthesis of 2-Halomethyl Dihydropyrroles and Mechanistic Insights into the Alkyl Halide Bond Formation
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