{"title":"基于聚二甲基硅氧烷（PDMS）微反应器的1,7-炔的可见光诱导串联环化制备菲那啶-6(5H)- 1","authors":"Dharavath Ravi, Vadla Shiva Prasad, Vadithya Ranga Rao, Silari Mohana Krishna, Chelukalapally Anil Kumar, Biswajit Saha, Praveen Reddy Adiyala","doi":"10.1002/cptc.202400332","DOIUrl":null,"url":null,"abstract":"<p>We report an organophotoredox-catalyzed visible-light-induced tandem cyclization of 1,7-enynes with diaryliodoniumtriflates has been established leading to Phenanthridin-6(5<i>H</i>)-one derivatives under metal-free conditions. This transformation is initiated by visible light induced aryl radical formation from diaryliodoniumtriflates, followed by its regioseletive addition to the acrylate moiety of 1,7-enynes then undergoes intramolecular <i>6-exo-dig</i> cascade radical annulation and which is terminated by single electron oxidation along with proton abstraction. This effective, sustainable and metal-free protocol exhibits a broad substrate scope and excellent tolerability towards various functional groups in good to excellent yields. Further implementation of a batch protocol to continuous flow protocol utilizing polydimethylsiloxane (PDMS) based microreactor exhibits its efficiency.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"9 4","pages":""},"PeriodicalIF":3.0000,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-Light-Induced Tandem Cyclization of 1,7-Enynes to Access Phenanthridin-6(5H)-Ones Using a Polydimethylsiloxane (PDMS) Based Microreactor\",\"authors\":\"Dharavath Ravi, Vadla Shiva Prasad, Vadithya Ranga Rao, Silari Mohana Krishna, Chelukalapally Anil Kumar, Biswajit Saha, Praveen Reddy Adiyala\",\"doi\":\"10.1002/cptc.202400332\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>We report an organophotoredox-catalyzed visible-light-induced tandem cyclization of 1,7-enynes with diaryliodoniumtriflates has been established leading to Phenanthridin-6(5<i>H</i>)-one derivatives under metal-free conditions. This transformation is initiated by visible light induced aryl radical formation from diaryliodoniumtriflates, followed by its regioseletive addition to the acrylate moiety of 1,7-enynes then undergoes intramolecular <i>6-exo-dig</i> cascade radical annulation and which is terminated by single electron oxidation along with proton abstraction. This effective, sustainable and metal-free protocol exhibits a broad substrate scope and excellent tolerability towards various functional groups in good to excellent yields. Further implementation of a batch protocol to continuous flow protocol utilizing polydimethylsiloxane (PDMS) based microreactor exhibits its efficiency.</p>\",\"PeriodicalId\":10108,\"journal\":{\"name\":\"ChemPhotoChem\",\"volume\":\"9 4\",\"pages\":\"\"},\"PeriodicalIF\":3.0000,\"publicationDate\":\"2024-12-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ChemPhotoChem\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cptc.202400332\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemPhotoChem","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cptc.202400332","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Visible-Light-Induced Tandem Cyclization of 1,7-Enynes to Access Phenanthridin-6(5H)-Ones Using a Polydimethylsiloxane (PDMS) Based Microreactor
We report an organophotoredox-catalyzed visible-light-induced tandem cyclization of 1,7-enynes with diaryliodoniumtriflates has been established leading to Phenanthridin-6(5H)-one derivatives under metal-free conditions. This transformation is initiated by visible light induced aryl radical formation from diaryliodoniumtriflates, followed by its regioseletive addition to the acrylate moiety of 1,7-enynes then undergoes intramolecular 6-exo-dig cascade radical annulation and which is terminated by single electron oxidation along with proton abstraction. This effective, sustainable and metal-free protocol exhibits a broad substrate scope and excellent tolerability towards various functional groups in good to excellent yields. Further implementation of a batch protocol to continuous flow protocol utilizing polydimethylsiloxane (PDMS) based microreactor exhibits its efficiency.
ChemPhotoChemChemistry-Physical and Theoretical Chemistry
CiteScore
5.80
自引率
5.40%
发文量
165
期刊介绍：
Light plays a crucial role in natural processes and leads to exciting phenomena in molecules and materials. ChemPhotoChem welcomes exceptional international research in the entire scope of pure and applied photochemistry, photobiology, and photophysics. Our thorough editorial practices aid us in publishing authoritative research fast. We support the photochemistry community to be a leading light in science.
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