Copper-Catalyzed Stepwise Aerobic Oxidation/N-Arylation from Benzothiazole

被引：0

作者：

Chen, Li ^{[1
]}

Li, Xuezhen ^{[1
]}

Xu, Keliang ^{[1
]}

Xu, Qi ^{[1
]}

Liu, Yan ^{[1
]}

Liu, Ping ^{[1
]}

机构：

[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832003, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 01期

基金：

中国国家自然科学基金;

关键词：

N-arylation; benzothiazoline; benzothiazolin-2-one; copper-catalyzed; oxidation; HYDROXYLATION; DERIVATIVES; EFFICIENT; LIGANDS; ARENES;

D O I：

10.1002/ejoc.202301108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein an efficient synthesis of 3-arylbenzothiazolin-2-one compounds. First, substituted benzothiazoles can be smoothly oxidized to benzothiazolin-2-one derivatives in the presence of CuCl2 and trifluoroacetic anhydride. Secondly, the Cu2S-catalyzed N-arylation of benzothiazolin-2-one with arylboronic acids yields a series of novel 3-aryl benzothiazolin-2-one derivatives. The method provides good yields for a variety of substrates and shows good compatibility with functional groups. The usefulness of the skeleton was further illustrated by the derivatization of 3-aryl-benzothiazolin-2-one. Mechanistic studies suggest that the oxidation of benzothiazole may undergo a free radical reaction process. An efficient synthesis of 3-arylbenzothiazolin-2-one compounds was achieved by Cu-catalyzed the oxidization of substituted benzothiazoles and N-arylation of benzothiazolin-2-one with arylboronic acids.image

引用

页数：5

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