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CuI/草酰胺催化(杂)芳基氯化物与酚的偶联反应合成二芳基醚。

CuI/Oxalamide Catalyzed Couplings of (Hetero)aryl Chlorides and Phenols for Diaryl Ether Formation.

机构信息

State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.

出版信息

Angew Chem Int Ed Engl. 2016 May 17;55(21):6211-5. doi: 10.1002/anie.201601035. Epub 2016 Apr 13.

DOI:10.1002/anie.201601035
PMID:27072902
Abstract

Couplings between (hetero)aryl chlorides and phenols can be effectively promoted by CuI in combination with an N-aryl-N'-alkyl-substituted oxalamide ligand to proceed smoothly at 120 °C. For this process, N-aryl-N'-alkyl-substituted oxalamides are more effective ligands than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides gave the corresponding coupling products in good yields. Satisfactory conversions were achieved with electron-rich phenols as well as a limited range of electron-poor phenols. Catalyst and ligand loadings as low as 1.5 mol % are sufficient for the scaled-up variants of some of these reactions.

摘要

(杂)芳基氯化物与酚的偶联可通过 CuI 与 N-芳基-N'-烷基取代的草酰胺配体的组合有效地促进,在 120°C 下顺利进行。对于该过程,N-芳基-N'-烷基取代的草酰胺是比双(N-芳基)取代的草酰胺更有效的配体。各种富电子和缺电子的芳基和杂芳基氯化物以良好的产率得到相应的偶联产物。富电子酚以及有限范围的缺电子酚也可获得令人满意的转化率。对于这些反应的一些放大变体,催化剂和配体的用量低至 1.5 mol%即可。

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