Yan-Ling Liu , Liu-Shuo Shi , Xian-Chen He , Jie Gao , Ke-Rong Li , Hao-Yue Xiang , Kai Chen , Hua Yang
{"title":"光氧化还原镍催化n -芳基丙烯酰胺与烷基溴的自由基环化。","authors":"Yan-Ling Liu , Liu-Shuo Shi , Xian-Chen He , Jie Gao , Ke-Rong Li , Hao-Yue Xiang , Kai Chen , Hua Yang","doi":"10.1039/d5ob00078e","DOIUrl":null,"url":null,"abstract":"<div><div>3,3-Disubstituted oxindoles constitute a significant class of biologically active molecules, often found in a wide range of bioactive compounds. In this work, we present a photoredox nickel-catalyzed intermolecular cyclization between <em>N</em>-arylacrylamides and readily accessible alkyl bromides, which affords a diverse range of 3,3-disubstituted oxindoles in moderate to high yields. Our mechanistic studies reveal that the reduction of alkyl bromides <em>via</em> single-electron transfer from a reactive Ni(<span>i</span>) species is a critical step in driving this radical cascade transformation. This approach offers several advantages, including mild reaction conditions, broad functional group tolerance, and a simple workup procedure.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3126-3130"},"PeriodicalIF":2.9000,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoredox nickel-catalyzed radical cyclization of N-arylacrylamides with alkyl bromides†\",\"authors\":\"Yan-Ling Liu , Liu-Shuo Shi , Xian-Chen He , Jie Gao , Ke-Rong Li , Hao-Yue Xiang , Kai Chen , Hua Yang\",\"doi\":\"10.1039/d5ob00078e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>3,3-Disubstituted oxindoles constitute a significant class of biologically active molecules, often found in a wide range of bioactive compounds. In this work, we present a photoredox nickel-catalyzed intermolecular cyclization between <em>N</em>-arylacrylamides and readily accessible alkyl bromides, which affords a diverse range of 3,3-disubstituted oxindoles in moderate to high yields. Our mechanistic studies reveal that the reduction of alkyl bromides <em>via</em> single-electron transfer from a reactive Ni(<span>i</span>) species is a critical step in driving this radical cascade transformation. This approach offers several advantages, including mild reaction conditions, broad functional group tolerance, and a simple workup procedure.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 13\",\"pages\":\"Pages 3126-3130\"},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2025-02-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052025001491\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025001491","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Photoredox nickel-catalyzed radical cyclization of N-arylacrylamides with alkyl bromides†
3,3-Disubstituted oxindoles constitute a significant class of biologically active molecules, often found in a wide range of bioactive compounds. In this work, we present a photoredox nickel-catalyzed intermolecular cyclization between N-arylacrylamides and readily accessible alkyl bromides, which affords a diverse range of 3,3-disubstituted oxindoles in moderate to high yields. Our mechanistic studies reveal that the reduction of alkyl bromides via single-electron transfer from a reactive Ni(i) species is a critical step in driving this radical cascade transformation. This approach offers several advantages, including mild reaction conditions, broad functional group tolerance, and a simple workup procedure.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.