CuI催化的酚与富电子对溴苯甲醚和缺电子间溴苯甲醚的O-芳基化反应研究

doi:10.6023/cjoc201301067

摘要/Abstract

报道碘化亚铜催化的酚与富电子的对溴苯甲醚与缺电子的间溴苯甲醚的O-芳基化反应. 研究发现缺电子的间溴苯甲醚在反应时表现出更高的反应活性, 而富电子的对溴苯甲醚反应活性较低. 通过提高反应温度和延长反应时间可使对溴苯甲醚发生O-芳基化反应, 产物的收率和缺电子的间溴苯甲醚相当. 用此方法成功合成了4-(4-氯苯氧基)苯甲醚, 并进一步合成了除草剂Clofop.

关键词: 交叉偶联, 富电子, 缺电子, CuI催化, O-芳基化

CuI-catalyzed O-arylation of phenols with electron-rich 4-bromoanisole and electron-deficient 3-bromoanisole was described. Electron-deficient 3-bromoanisole showed high reactivity, and electron-rich 4-bromoanisole had low reactivity. O-Arylation of 4-bromoanisole occurred to afford the product by increasing reaction temperature and time. This reaction was applied to the synthesis of 1-chloro-4-(4-methoxyphenoxy)benzene, which was further synthesized to herbicide Clofop.

Key words: cross-coupling, electron-rich, electron-deficient, CuI-catalyzed, O-arylation

引用此文

杏朝刚, 俞建忠, 张培志, 吴军. CuI催化的酚与富电子对溴苯甲醚和缺电子间溴苯甲醚的O-芳基化反应研究[J]. 有机化学, 2013, 33(04): 840-847.

Xing Chaogang, Yu Jianzhong, Zhang Peizhi, Wu Jun. CuI-Catalyzed O-Arylation of Phenols with Electron-Rich 4-Bromoanisole and Electron-Deficient 3-Bromoanisole[J]. Chin. J. Org. Chem., 2013, 33(04): 840-847.

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