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Updated: Jul 17, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Formal Halogen Transfer of Bromoarenes via Stepwise Reactions
Kengo Inoue1, Atsunori Mori1,2, Kentaro Okano1
1Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan.
Abstract:
A two-step halogen transfer of bromoarenes is reported. Mono-, di-, and tribromoaryllithiums generated through deprotonative lithiation were converted into organozinc species by in situ zincation, which were then subjected to bromination to provide the corresponding di-, tri-, and tetrabromoarenes, respectively, in 41-95% yields. Regioselective bromine-magnesium exchange with ethylmagnesium chloride followed by electrophilic trapping afforded benzene, pyridine, quinoline, pyrimidine, and thiazole derivatives with the bromo group translocated from the original position in 28-86% yields.
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