{"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":"<p><p>An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF<sub>2</sub>H-substituted benzimidazo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-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.</p>","PeriodicalId":2,"journal":{"name":"ACS Applied Bio Materials","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoredox-catalysed radical difluoromethylation/cyclization of <i>N</i>-acryloyl-2-arylbenzimidazole to access CF<sub>2</sub>H-substituted benzimidazo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-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\":\"<p><p>An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF<sub>2</sub>H-substituted benzimidazo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-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.</p>\",\"PeriodicalId\":2,\"journal\":{\"name\":\"ACS Applied Bio Materials\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-10-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Applied Bio Materials\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4ob01413h\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"MATERIALS SCIENCE, BIOMATERIALS\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Bio Materials","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01413h","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, BIOMATERIALS","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.