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Electrophilic Cyclizations of Diaryl-2,3-allenyl Ethers with N‑Bromosuccinimide: En Route to 2‑Bromonaphthalenes

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posted on 03.10.2014, 00:00 authored by Minyan Wang, Jing Li, Chunling Fu, Shengming Ma
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.