Yakura Takayuki, Tian Yuan, Yamauchi Yû, Omoto Masanori, Konishi Tatsuya
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan.
Chem Pharm Bull (Tokyo). 2009 Mar;57(3):252-6. doi: 10.1248/cpb.57.252.
A catalytic hypervalent iodine oxidation of p-alkoxyphenols using 4-iodophenoxyacetic acid (1a) and Oxone((R)) was developed. Reaction of p-alkoxyphenol (2) with a catalytic amount of 1a in the presence of Oxone((R)) as a co-oxidant in 2,2,2-trifluoroethanol-water (1 : 2) gave the corresponding p-quinone (3) in excellent yield without special operation. The substituent effect on iodobenzene ring in the oxidation was observed; p-alkoxy is the most effective, with the series following the approximate order p-RO>p-Me, o-MeO, m-MeO>H>o-CO(2)H. And remarkable solvent effects were observed.
开发了一种使用4-碘苯氧基乙酸（1a）和过硫酸氢钾复合盐（Oxone((R))）对对烷氧基苯酚进行催化高价碘氧化的方法。对烷氧基苯酚（2）与催化量的1a在过硫酸氢钾复合盐（Oxone((R))）作为共氧化剂存在下，于2,2,2-三氟乙醇-水（1:2）中反应，无需特殊操作即可以优异的产率得到相应的对醌（3）。观察到氧化反应中碘苯环上的取代基效应；对烷氧基是最有效的，其顺序大致为对-RO＞对-Me、邻-MeO、间-MeO＞H＞邻-CO₂H。并且观察到了显著的溶剂效应。
