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铜(II)催化卤代芳烃的羟化反应,使用甘醇酸作为配体。

Copper(II)-catalyzed hydroxylation of aryl halides using glycolic acid as a ligand.

机构信息

Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China.

出版信息

J Org Chem. 2013 Jun 7;78(11):5804-9. doi: 10.1021/jo400702z. Epub 2013 May 28.

DOI:10.1021/jo400702z
PMID:23713792
Abstract

Copper(II)-catalyzed hydroxylation of aryl halides has been developed to afford functionalized phenols. The protocol utilizes the reagent combination of Cu(OH)2, glycolic acid, and NaOH in aqueous DMSO, all of which are cheap, readily available, and easily removable after the reaction. A broad range of aryl iodides and activated aryl bromides were transformed into the corresponding phenols in excellent yields. Moreover, it has been shown that C-O(alkyl)-coupled product, instead of phenol, can be predominantly formed under similar reaction conditions.

摘要

铜(II)催化的芳基卤化物的羟化反应已经被开发出来,以提供官能化的酚类化合物。该方案利用 Cu(OH)2、乙醇酸和 NaOH 在水溶液中的试剂组合,所有这些试剂都很便宜、易得,并且在反应后很容易去除。广泛的芳基碘化物和活化的芳基溴化物都以优异的收率转化为相应的酚类化合物。此外,已经表明,在类似的反应条件下,C-O(烷基)偶联产物而不是酚可以主要形成。

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