Timothée Cadart, Lucia Feriancová, Petr Henke, Robert Gyepes, Ivana Císařová, Květa Kalíková, Martin Kotora
{"title":"Synthesis of highly fluorescent helical quinolizinium salts by a Rh-catalyzed cyclotrimerization/C-H activation sequence.","authors":"Timothée Cadart, Lucia Feriancová, Petr Henke, Robert Gyepes, Ivana Císařová, Květa Kalíková, Martin Kotora","doi":"10.1039/d4cc06512c","DOIUrl":null,"url":null,"abstract":"<p><p>A series of helical quinolizinium salts were prepared utilizing Rh-catalyzed [2+2+2]cyclotrimerization and C-H activation processes as the crucial synthetic steps. The cyclotrimerization of appropriately substituted diynes with trimethylsilylethyne under Rh-catalyzed conditions provided the 1-arylisoquinolines in up to 61% isolated yields. Their Rh-catalyzed C-H activation/annulation with various aryl and alkyl disubstituted alkynes gave rise to [7]-helical quinolizinium salts in high isolated yields (up to 93%). Enantioselective C-H activation was also tried with asymmetric induction up to 62% ee. The respective boron and platinum complexes of 1-arylisoquinolines were prepared as well. All prepared compounds exhibit fluorescence in the orange-red light region (606-682 nm) with <i>Φ</i><sub>Fs</sub> 28-99%.</p>","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":" ","pages":""},"PeriodicalIF":4.3000,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4cc06512c","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A series of helical quinolizinium salts were prepared utilizing Rh-catalyzed [2+2+2]cyclotrimerization and C-H activation processes as the crucial synthetic steps. The cyclotrimerization of appropriately substituted diynes with trimethylsilylethyne under Rh-catalyzed conditions provided the 1-arylisoquinolines in up to 61% isolated yields. Their Rh-catalyzed C-H activation/annulation with various aryl and alkyl disubstituted alkynes gave rise to [7]-helical quinolizinium salts in high isolated yields (up to 93%). Enantioselective C-H activation was also tried with asymmetric induction up to 62% ee. The respective boron and platinum complexes of 1-arylisoquinolines were prepared as well. All prepared compounds exhibit fluorescence in the orange-red light region (606-682 nm) with ΦFs 28-99%.
期刊介绍:
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