CuI-Catalyzed O-Arylation of Phenols with Electron-Rich 4-Bromoanisole and Electron-Deficient 3-Bromoanisole

doi:10.6023/cjoc201301067

Abstract

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

Cite this article

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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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