Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-06-12 DOI:10.1039/d4qo00858h

Lin Zhao, Xinyu Zhou, Kemeng Zhang, Siyu Han, Ge Wu

引用次数: 0

Abstract

Herein, we describe an electrochemical strategy that enables the aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na, providing an unprecedented route to access S-CD3 isothioureas in satisfactory yields. Mechanistic studies reveal that the transformation initiates the addition of CD3S radical to the isocyanide followed by a nucleophilic attack of the in-situ generated imine carbocation intermediate with anilines. Importantly, these reactions exhibit exclusive chemo-selectivity at carbon of isocyanides, wide functional groups compatibility as well as late-stage functionalization of complex substrates.

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异氰酸酯与苯胺和 CD3SSO3Na 的电化学氨基三甲基硫代反应

在本文中，我们介绍了一种电化学策略，该策略可实现异氰酸酯与苯胺和 CD3SSO3Na 的氨三甲硫醇化反应，为以令人满意的产率获得 S-CD3 异硫脲提供了一条前所未有的途径。机理研究表明，这种转化首先是 CD3S 自由基与异氰酸酯发生加成反应，然后原位生成的亚胺羰基中间体与苯胺发生亲核反应。重要的是，这些反应在异氰酸酯的碳上表现出独特的化学选择性、广泛的官能团兼容性以及复杂底物的后期官能化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.