Synthesis of amides via TBN-induced oxidation cross-coupling of acetonitrile and N-sulfinylanilines

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-05-03 DOI:10.1080/00397911.2025.2494245

Quansen Wu (Methodology Writing – review & editing) , Zizhong Ma (Data curation) , Rui Li (Methodology) , Ruiqiang Shang (Methodology) , Zhenyu An (Writing – original draft) , Yafeng Liu (Writing – original draft) , Qing Huang (Writing – review & editing) , Zhenjie Qi (Conceptualization Funding acquisition Project administration Writing – original draft Writing – review & editing)

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引用次数: 0

Abstract

A novel method for the synthesis of amides has been developed that features – tert-butyl nitrite-induced oxidative cross-coupling of acetonitrile with N-sulfinylanilines. Acetonitrile serves as the C2 building block in this process. The present protocol effectively inhibits the competition with the C≡N triple bond but enables the in situ formation of unsaturated C–O bond. The reaction demonstrates a broad substrate scope and can be conducted under mild conditions. Mechanistic studies, including radical trapping experiments and H₂¹⁸O-labeling, confirm a radical-mediated pathway involving acetonitrile-derived intermediates. Additionally, this method is amenable to gram-scale synthesis.

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乙腈与n -亚砜苯胺的tbn诱导氧化交偶联合成酰胺

提出了一种以亚硝酸盐叔丁基诱导乙腈与n -亚砜苯胺氧化交偶联为特征的酰胺合成新方法。在这个过程中，乙腈作为C2的组成部分。目前的协议有效地抑制了与C≡N三键的竞争，但使原位形成不饱和的C - o键成为可能。该反应底物范围广，可在温和条件下进行。机制研究，包括自由基捕获实验和h218o标记，证实了一个涉及乙腈衍生中间体的自由基介导途径。此外，该方法适用于克级合成。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.