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芳烃促进硫代酰胺的脱硫化氢反应:制备腈和二芳基硫醚

Arynes Promoted Dehydrosulfurization of Thioamides: Access to Nitriles and Diaryl Sulfides.

作者信息

Liu Cuicui, Cai Zhihua, Luo Jinyun, Wu Leifang, He Lin

机构信息

School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi 832003, P. R. China.

Analysis and Testing Center of Shihezi University, Xinjiang Uygur Autonomous Region, 832000, P. R. China.

出版信息

Org Lett. 2024 Sep 13;26(36):7678-7682. doi: 10.1021/acs.orglett.4c02796. Epub 2024 Aug 30.

Abstract

An aryne-promoted dehydrosulfurization reaction of thioamides to give nitriles and diaryl sulfides in a one-pot manner is presented. Aromatic, heteroaromatic, and aliphatic natural products and drug-derived nitriles and diaryl sulfides were obtained in good to excellent yields. Especially, selenoamide was also a suitable substrate and produced diaryl selenide and nitrile in high yields. The D-labeled experiments indicated that the protons of thioamides transfer to diaryl sulfides.

摘要

本文报道了一种通过芳炔促进硫代酰胺的脱氢脱硫反应,以一锅法制备腈和二芳基硫醚的方法。该方法能以良好至优异的产率得到芳香族、杂芳香族和脂肪族天然产物以及药物衍生的腈和二芳基硫醚。特别地,硒代酰胺也是合适的底物,能高产率地生成二芳基硒醚和腈。氘标记实验表明硫代酰胺的质子转移至二芳基硫醚。

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