{"title":"光氧化催化的 N-丙烯酰基-2-芳基苯并咪唑自由基二氟甲基化/环化反应,获得 CF2H 取代的苯并咪唑并[2,1-a]异喹啉-6(5H)-酮。","authors":"Jinwei Yuan , Hongzhao Qu , Wenfeng Jia , Jinling Li , Liangru Yang , Yongmei Xiao , Yanli Yin , Lingbo Qu","doi":"10.1039/d4ob01413h","DOIUrl":null,"url":null,"abstract":"<div><div>An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF<sub>2</sub>H-substituted benzimidazo[2,1-<em>a</em>]isoquinolin-6(5<em>H</em>)-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the –CF<sub>2</sub>H group under mild conditions. This protocol utilized an easily accessible and inexpensive organophotocatalyst, offering the benefits of a broad substrate scope, good functional group tolerance, and good to excellent yields, in addition to a simple operational procedure. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that a radical pathway constitutes a single electron transfer (SET) procedure.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 45","pages":"Pages 8904-8915"},"PeriodicalIF":2.9000,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoredox-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones†\",\"authors\":\"Jinwei Yuan , Hongzhao Qu , Wenfeng Jia , Jinling Li , Liangru Yang , Yongmei Xiao , Yanli Yin , Lingbo Qu\",\"doi\":\"10.1039/d4ob01413h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF<sub>2</sub>H-substituted benzimidazo[2,1-<em>a</em>]isoquinolin-6(5<em>H</em>)-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the –CF<sub>2</sub>H group under mild conditions. This protocol utilized an easily accessible and inexpensive organophotocatalyst, offering the benefits of a broad substrate scope, good functional group tolerance, and good to excellent yields, in addition to a simple operational procedure. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that a radical pathway constitutes a single electron transfer (SET) procedure.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 45\",\"pages\":\"Pages 8904-8915\"},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-10-09\",\"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/S147705202400911X\",\"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/S147705202400911X","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Photoredox-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones†
An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the –CF2H group under mild conditions. This protocol utilized an easily accessible and inexpensive organophotocatalyst, offering the benefits of a broad substrate scope, good functional group tolerance, and good to excellent yields, in addition to a simple operational procedure. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that a radical pathway constitutes a single electron transfer (SET) 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.