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Reductive Halogenation Reactions: Selective Synthesis of Unsymmetrical α-Haloketones

Zhiqi Lao, Huimiao Zhang and Patrick H. Toy*

*Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China, Email: phtoyhku.hk

Z. Lao, H. Zhang, P. H. Toy, Org. Lett., 2019, 21, 8149-8152.

DOI: 10.1021/acs.orglett.9b02324 (free Supporting Information)


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Abstract

A triphenylphosphine oxide catalyzed reductive halogenation of an α,β-unsaturated ketone with trichlorosilane as the reducing reagent and an N-halosuccinimide as the electrophilic halogen source enables a selective synthesis of unsymmetrical α-haloketones.

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Key Words

Wittig reaction, enones, bromination, trichlorosilane, NBS


ID: J54-Y2019