Visible Light‐Promoted Cascade Sulfonylation‐Cyclization‐Aromatization of Tertiary Enamides to Access Multi‐Substituted Pyridines and 1,2‐Dihydropyridines

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-04-15 DOI:10.1002/adsc.202401516

Xin‐Ming Xu , Jiping Wang , Sen Chen , Xiaoxu Chen , Jinchun Chen , Qian Liu , Zu‐Li Wang , Miao Tian , Kai Sun

引用次数: 0

Abstract

Functionalized pyridines and 1,2‐dihydropyridines are crucial organic entities in natural products, organic materials, drugs and catalysts. Despite progress, a facile and eco‐friendly synthesis remains desirable so far. In this context, we disclose a novel visible light‐promoted radical cascade sulfonylation‐cyclization‐aromatization of N‐propargyl enamides with selenosulfonates. This approach avoids the use of metal‐ or photocatalyst, bases and external oxidants, marking a significant advance in sustainable and green chemistry accords. Utilizing this protocol, we successfully synthesized a diverse range of sulfonated 1,2‐dihydropyridines and pyridines, featuring good functional group compatibility, simple operation and mild condition.

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可见光促进三级烯酰胺的级联磺酰化-环化-芳香化反应以获得多取代吡啶和 1,2-二氢吡啶

功能化吡啶和1,2-二氢吡啶是天然产物、有机材料、药物和催化剂中重要的有机实体。尽管取得了进展，但到目前为止，一种简单而环保的合成方法仍然是可取的。在此背景下，我们揭示了一种新的可见光促进的n-丙炔酰胺与硒代磺酸盐的磺化-环化-芳构化自由基级联反应。这种方法避免使用金属或光催化剂、碱和外部氧化剂，标志着可持续和绿色化学协议的重大进步。利用该工艺，我们成功合成了多种磺化的1,2-二氢吡啶和吡啶，具有官能团相容性好、操作简单、条件温和等特点。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.