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铜催化肟乙酸盐和黄原酸盐在氧化还原中性条件下合成噻唑-2-基醚。

Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions.

机构信息

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.

出版信息

Chem Commun (Camb). 2018 Apr 10;54(30):3767-3770. doi: 10.1039/c8cc00445e.

DOI:10.1039/c8cc00445e
PMID:29589845
Abstract

A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.

摘要

一种新型的铜催化肟乙酸盐和黄原酸盐的环化反应,用于合成具有显著区域选择性的噻唑-2-基醚,已经被开发出来。各种肟乙酸盐,无论是衍生自芳基酮还是烷基酮,还是天然产物核心,都适合这种转化。当两个反应位点都是亚甲基时,也得到了独特的二氢噻唑。机理研究表明,亚氨基铜(III)中间体参与了反应。此外,该反应在氧化还原中性条件下进行,不需要添加物或配体。

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