铑催化环碘酰化2-吡啶酮的定向C-H杂芳化反应

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI:10.1002/ejoc.202500306

Zhan‐Wei Fu , Shi Cao , Mu‐Peng Luo , Shu‐Rong Ban , Shou‐Guo Wang

{"title":"铑催化环碘酰化2-吡啶酮的定向C-H杂芳化反应","authors":"Zhan‐Wei Fu , Shi Cao , Mu‐Peng Luo , Shu‐Rong Ban , Shou‐Guo Wang","doi":"10.1002/ejoc.202500306","DOIUrl":null,"url":null,"abstract":"<div><div>2‐Pyridone is a crucial building block in bioactive natural products and serves as a vital intermediate for the synthesis of bioactive nitrogen‐containing heterocycles. Recent advancements in transition‐metal‐catalyzed C–H functionalization have enabled the direct modification of 2‐pyridones, circumventing the need for prefunctionalization. Herein, a Rh(III)‐catalyzed, C6‐selective C–H heteroarylation of 2‐pyridones using cyclic iodonium ylides as carbene precursors is reported. The versatility and broad applicability of this method are demonstrated through the efficient synthesis of diverse compounds featuring both 2‐pyridone‐pyridine and cyclic 1,3‐dicarbonyl derivatives.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500306"},"PeriodicalIF":2.7000,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rhodium‐Catalyzed Directed C–H Heteroarylation of 2‐Pyridones Using Cyclic Iodonium Ylides\",\"authors\":\"Zhan‐Wei Fu , Shi Cao , Mu‐Peng Luo , Shu‐Rong Ban , Shou‐Guo Wang\",\"doi\":\"10.1002/ejoc.202500306\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>2‐Pyridone is a crucial building block in bioactive natural products and serves as a vital intermediate for the synthesis of bioactive nitrogen‐containing heterocycles. Recent advancements in transition‐metal‐catalyzed C–H functionalization have enabled the direct modification of 2‐pyridones, circumventing the need for prefunctionalization. Herein, a Rh(III)‐catalyzed, C6‐selective C–H heteroarylation of 2‐pyridones using cyclic iodonium ylides as carbene precursors is reported. The versatility and broad applicability of this method are demonstrated through the efficient synthesis of diverse compounds featuring both 2‐pyridone‐pyridine and cyclic 1,3‐dicarbonyl derivatives.</div></div>\",\"PeriodicalId\":167,\"journal\":{\"name\":\"European Journal of Organic Chemistry\",\"volume\":\"28 35\",\"pages\":\"Article e202500306\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-09-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"European Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1434193X25005109\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X25005109","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

2-吡啶酮是生物活性天然产物的重要组成部分，是合成生物活性含氮杂环的重要中间体。最近在过渡金属催化的碳氢功能化方面取得的进展使2-吡啶酮的直接修饰成为可能，而不需要预功能化。在这项研究中，我们报道了Rh（III）催化的，c6选择性的2-吡啶酮的C-H杂芳化反应，使用环碘酰化物作为碳前体。该方法的通用性和广泛适用性通过高效合成具有2-吡啶酮-吡啶和环1,3-二羰基衍生物的各种化合物得到证明。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Rhodium‐Catalyzed Directed C–H Heteroarylation of 2‐Pyridones Using Cyclic Iodonium Ylides

查看原文本刊更多论文

Rhodium‐Catalyzed Directed C–H Heteroarylation of 2‐Pyridones Using Cyclic Iodonium Ylides

2‐Pyridone is a crucial building block in bioactive natural products and serves as a vital intermediate for the synthesis of bioactive nitrogen‐containing heterocycles. Recent advancements in transition‐metal‐catalyzed C–H functionalization have enabled the direct modification of 2‐pyridones, circumventing the need for prefunctionalization. Herein, a Rh(III)‐catalyzed, C6‐selective C–H heteroarylation of 2‐pyridones using cyclic iodonium ylides as carbene precursors is reported. The versatility and broad applicability of this method are demonstrated through the efficient synthesis of diverse compounds featuring both 2‐pyridone‐pyridine and cyclic 1,3‐dicarbonyl derivatives.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.