{"title":"可见光诱导的 N-芳基肉桂酰胺自催化氟烷基化/环化反应:含氟烷基的 3,4-二取代二氢-1,5-萘啶-2(1H)-酮和 7,8-二取代二氢吡啶并[3,2-d]嘧啶-6(5H)-酮的合成","authors":"Hongmiao Yao, Qianding Zeng, Yiqun Tang, Xiangqiao Yang, Shaodong Wang, Jiangmeng Ren and Bu-Bing Zeng","doi":"10.1039/D4NJ01975J","DOIUrl":null,"url":null,"abstract":"<p >A novel visible-light-mediated fluoroalkylation/cyclization tandem process for constructing fluoroalkyl-containing 3,4-disubstituted dihydro-1,5-naphthyridin-2(1<em>H</em>)-ones and 7,8-disubstituted dihydropyrido[3,2-<em>d</em>]pyrimidin-6(5<em>H</em>)-ones has been explored. This method is compatible with a wide range of <em>N</em>-arylcinnamamides as well as sodium fluoroalkylsulfonates (RfSO<small><sub>2</sub></small>Na, Rf = CHF<small><sub>2</sub></small>, CF<small><sub>3</sub></small>, C<small><sub>4</sub></small>F<small><sub>9</sub></small>, C<small><sub>6</sub></small>F<small><sub>13</sub></small>) and avoids the need for any external oxidant or photocatalyst. Mechanism studies revealed that the singlet oxygen coexists with the superoxide radical anion through energy transfer and single electron transfer processes during the photoredox reaction.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7000,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-light-induced self-catalyzed fluoroalkylation/cyclization of N-arylcinnamamides: synthesis of fluoroalkyl-containing 3,4-disubstituted dihydro-1,5-naphthyridin-2(1H)-ones and 7,8-disubstituted dihydropyrido[3,2-d]pyrimidin-6(5H)-ones†\",\"authors\":\"Hongmiao Yao, Qianding Zeng, Yiqun Tang, Xiangqiao Yang, Shaodong Wang, Jiangmeng Ren and Bu-Bing Zeng\",\"doi\":\"10.1039/D4NJ01975J\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A novel visible-light-mediated fluoroalkylation/cyclization tandem process for constructing fluoroalkyl-containing 3,4-disubstituted dihydro-1,5-naphthyridin-2(1<em>H</em>)-ones and 7,8-disubstituted dihydropyrido[3,2-<em>d</em>]pyrimidin-6(5<em>H</em>)-ones has been explored. This method is compatible with a wide range of <em>N</em>-arylcinnamamides as well as sodium fluoroalkylsulfonates (RfSO<small><sub>2</sub></small>Na, Rf = CHF<small><sub>2</sub></small>, CF<small><sub>3</sub></small>, C<small><sub>4</sub></small>F<small><sub>9</sub></small>, C<small><sub>6</sub></small>F<small><sub>13</sub></small>) and avoids the need for any external oxidant or photocatalyst. Mechanism studies revealed that the singlet oxygen coexists with the superoxide radical anion through energy transfer and single electron transfer processes during the photoredox reaction.</p>\",\"PeriodicalId\":95,\"journal\":{\"name\":\"New Journal of Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-07-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"New Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj01975j\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj01975j","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Visible-light-induced self-catalyzed fluoroalkylation/cyclization of N-arylcinnamamides: synthesis of fluoroalkyl-containing 3,4-disubstituted dihydro-1,5-naphthyridin-2(1H)-ones and 7,8-disubstituted dihydropyrido[3,2-d]pyrimidin-6(5H)-ones†
A novel visible-light-mediated fluoroalkylation/cyclization tandem process for constructing fluoroalkyl-containing 3,4-disubstituted dihydro-1,5-naphthyridin-2(1H)-ones and 7,8-disubstituted dihydropyrido[3,2-d]pyrimidin-6(5H)-ones has been explored. This method is compatible with a wide range of N-arylcinnamamides as well as sodium fluoroalkylsulfonates (RfSO2Na, Rf = CHF2, CF3, C4F9, C6F13) and avoids the need for any external oxidant or photocatalyst. Mechanism studies revealed that the singlet oxygen coexists with the superoxide radical anion through energy transfer and single electron transfer processes during the photoredox reaction.