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铜催化的富含电子芳环与对甲苯磺酸的区域选择性 C-H 磺酰化反应及芳基(均三甲苯基)碘𬭩磺酸盐的磺酰化反应。

Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with p-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates.

机构信息

College of Chemistry and Materials Science, Sichuan Normal University , Chengdu 610068, People's Republic of China.

出版信息

J Org Chem. 2017 Mar 17;82(6):3094-3101. doi: 10.1021/acs.joc.7b00081. Epub 2017 Mar 7.

Abstract

Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions.

摘要

发展了一种铜催化的对甲苯磺酸促进的富电子芳环 C-H 磺酰化反应。富电子苯衍生物和杂芳环可以进行这种 C-H 磺酰化反应,生成芳基对甲苯磺酸酯。此外,还研究了芳基(均三甲苯基)碘𬭩磺酸盐的磺酰化反应。芳基(均三甲苯基)碘𬭩对甲苯磺酸酯和三氟甲磺酸酯都可以顺利反应得到芳基磺酸酯。生成的芳基磺酸酯可以转化为苯酚,也可以作为偶联反应的良好配体。

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