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

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• 作者：Minyan Wang ; Jing Li ; Chunling Fu ; Shengming Ma
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：October 3, 2014
• 年：2014
• 卷：16
• 期：19
• 页码：4976-4979
• 全文大小：498K
• ISSN：1523-7052

文摘

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鈥?6% 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.