Synthesis of <i>meta</i>-arylphenol derivatives <i>via</i> acid-promoted rearrangement of cyclohexadienones
作者:Hongyan Xie、Minxiang Zhang、Xueyu Fang、Zhaohua Yan、Hua Yao
DOI:10.1039/d3ob01363d
日期:——
A highly effective strategy for the synthesis of meta-arylphenol derivatives through the selective rearrangement of 4-alkyl-4-aryl-2,5-cyclohexadienones under metal-free conditions was developed, in which acid-promoted [1,2]-migration of the aryl group at C-4 occurred exclusively when the alkyl group at C-4 was a methyl group. Treatment of 4-methyl-4-aryl-2,5-cyclohexadienones with 37% HCl in Ac2O
开发了一种在无金属条件下通过 4-烷基-4-芳基-2,5-环己二烯酮选择性重排合成间芳基苯酚衍生物的高效策略,其中酸促进[1,2] -迁移仅当C-4处的烷基是甲基时,才会发生C-4处的芳基的取代。在室温下,用 37% HCl 的 Ac 2 O溶液处理 4-甲基-4-芳基-2,5-环己二烯酮,得到多取代间芳基苯基乙酸酯,产率 75-94%。还描述了该方案在多环芳香族化合物合成中的应用。