Sabyasachi Manna , Rahul Halanuru Sreedhara , Kandikere Ramaiah Prabhu
{"title":"可见光介导的芳基异氰酸酯与三羰基的自由基加成级联环化反应:快速获得取代的菲啶类和异喹啉类化合物。","authors":"Sabyasachi Manna , Rahul Halanuru Sreedhara , Kandikere Ramaiah Prabhu","doi":"10.1039/d4ob01405g","DOIUrl":null,"url":null,"abstract":"<div><div>A visible light-mediated synthesis of substituted phenanthridines and isoquinolines from <em>ortho</em>-substituted aryl isocyanides and tricarbonyl compounds is unveiled <em>via</em> the radical addition cascade cyclization (RACC) strategy. This acid/base-free method involves an oxidant (a persulphate salt) and a Ru-photocatalyst. This protocol avoids the use of halogenated compounds as pre-functionalized carbonyl precursors. The products can be easily post-modified to other important small molecules. The functional group tolerance of the reaction and the yields of the products are good without any scalability issues. The mechanistic investigation suggested the presence of a radical pathway during the reaction.</div></div>","PeriodicalId":2,"journal":{"name":"ACS Applied Bio Materials","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible light-mediated radical addition cascade cyclization of aryl isocyanides with tricarbonyls: rapid access to substituted phenanthridines and isoquinolines†\",\"authors\":\"Sabyasachi Manna , Rahul Halanuru Sreedhara , Kandikere Ramaiah Prabhu\",\"doi\":\"10.1039/d4ob01405g\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A visible light-mediated synthesis of substituted phenanthridines and isoquinolines from <em>ortho</em>-substituted aryl isocyanides and tricarbonyl compounds is unveiled <em>via</em> the radical addition cascade cyclization (RACC) strategy. This acid/base-free method involves an oxidant (a persulphate salt) and a Ru-photocatalyst. This protocol avoids the use of halogenated compounds as pre-functionalized carbonyl precursors. The products can be easily post-modified to other important small molecules. The functional group tolerance of the reaction and the yields of the products are good without any scalability issues. The mechanistic investigation suggested the presence of a radical pathway during the reaction.</div></div>\",\"PeriodicalId\":2,\"journal\":{\"name\":\"ACS Applied Bio Materials\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-10-02\",\"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://www.sciencedirect.com/org/science/article/pii/S147705202400795X\",\"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://www.sciencedirect.com/org/science/article/pii/S147705202400795X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, BIOMATERIALS","Score":null,"Total":0}
Visible light-mediated radical addition cascade cyclization of aryl isocyanides with tricarbonyls: rapid access to substituted phenanthridines and isoquinolines†
A visible light-mediated synthesis of substituted phenanthridines and isoquinolines from ortho-substituted aryl isocyanides and tricarbonyl compounds is unveiled via the radical addition cascade cyclization (RACC) strategy. This acid/base-free method involves an oxidant (a persulphate salt) and a Ru-photocatalyst. This protocol avoids the use of halogenated compounds as pre-functionalized carbonyl precursors. The products can be easily post-modified to other important small molecules. The functional group tolerance of the reaction and the yields of the products are good without any scalability issues. The mechanistic investigation suggested the presence of a radical pathway during the reaction.