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在水中高效合成有机硫代乙酸酯。

Efficient synthesis of organic thioacetates in water.

机构信息

Dipartimento di Scienze della Salute, Università Magna Græcia, Viale Europa, Germaneto, CZ, Italy.

Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Edificio Polifunzionale, Università della Calabria, 87030 Arcavacata di Rende, Cosenza, Italy.

出版信息

Org Biomol Chem. 2018 Nov 7;16(41):7753-7759. doi: 10.1039/c8ob01896k. Epub 2018 Oct 9.

DOI:10.1039/c8ob01896k
PMID:30299446
Abstract

Thioacetates as precursors of thiols are interesting starting points for synthesizing other organosulfur compounds. Herein, we propose a simple, efficient and fast method to obtain organic thioacetates using water as a solvent. Taking into account the great attention that has been paid toward environmentally friendly synthetic procedures in the past decades, we prove the role and the strength of the thioacetate anion as a nucleophile for nucleophilic displacement reactions in an aqueous medium. The reactions were carried out under pH control, to prevent the decomposition of the mesylate starting materials, using potassium carbonate as a safe and mild base. A simple work up allows products to be obtained with excellent yield and acceptable purity.

摘要

硫代乙酸盐作为硫醇的前体,是合成其他有机硫化合物的有趣起点。在此,我们提出了一种使用水作为溶剂来获得有机硫代乙酸盐的简单、高效和快速的方法。考虑到过去几十年中人们对环保合成方法的极大关注,我们证明了硫代乙酸盐阴离子作为亲核试剂在水介质中进行亲核取代反应的作用和强度。反应在 pH 控制下进行,以防止甲磺酸酯起始原料分解,使用碳酸钾作为安全温和的碱。简单的后处理可以获得产率优异、纯度可接受的产物。

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