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硫酯、硫代氨基甲酸酯和硫代酰胺的催化氢化。

Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides.

出版信息

J Am Chem Soc. 2020 Dec 30;142(52):21628-21633. doi: 10.1021/jacs.0c10884. Epub 2020 Dec 17.

DOI:10.1021/jacs.0c10884
PMID:33332968
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7775745/
Abstract

Direct hydrogenation of thioesters with H provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.

摘要

用 H 直接氢化硫酯为醇和硫醇的合成提供了一种简便、无浪费的方法。然而,目前还没有关于该反应的报道,可能是因为生成的硫醇与典型的氢化催化剂不相容。在这里,我们报告了一种高效和选择性的硫酯氢化反应。该反应由基于吖啶的钌配合物催化,无需添加任何助剂。各种硫酯都被完全氢化,生成相应的醇和硫醇,对酰胺、酯和羧酸基团具有很好的耐受性。硫代氨基甲酸酯和硫代酰胺也可以在类似的条件下进行氢化,大大扩展了有机硫化合物氢化的应用范围。

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