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Updated: Apr 23, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Electrophilic cyclizations of diaryl-2,3-allenyl ethers with N-bromosuccinimide: en route to 2-bromonaphthalenes
Minyan Wang1, Jing Li, Chunling Fu
1Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University , Hangzhou 310027, Zhejiang, People's Republic of China.
Abstract:
The reaction of diaryl-2,3-allenyl ethers with N-bromosuccinimide in a mixed solvent of CH3NO2/EtOH affords highly functionalized 2-bromonaphthalenes in 21-66% yields. The electronic effect on the aryl is important to the selectivity of the reaction: when 4-(trifluoromethyl)phenyl or 1-naphthyl was applied as one of the two aryl groups, the regioselectivity was practical, affording the products with the other relatively electron-rich phenyl ring or the non-1-naphthyl group being cyclized as the major, respectively.
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