{"title":"Redox-Neutral Cascade Trifluoromethylation of Dienes and Enynes using a Perylene Diimide (PDI) Organophotocatalyst","authors":"Krishna Gopal Ghosh, Koustav Pal, Manasi Mallick, Debabrata Das, Devarajulu Sureshkumar","doi":"10.1002/adsc.202401040","DOIUrl":null,"url":null,"abstract":"The Perylene diimide (PDI) is an underexplored synthetic organic dye with significant potential in photoredox catalysis. We have developed a good chemo- and regioselective, atom-economical methodology for synthesizing trifluoroethylated saturated heterocyclic derivatives and trifluoroethyl-containing cyclobutane derivatives. This process involves the generation of trifluoromethyl radical from the Langlois (CF<sub>3</sub>SO<sub>2</sub>Na) reagent under photoredox conditions, which selectively reacts with the electron-rich terminal double/triple bonds in the diene/enyne framework. The resulting intermediate undergoes a cascade cyclization, yielding the desired compounds in a redox-neutral manner. Our methodology operates under very mild conditions, eliminating the need for transition metals and external oxidizing agents. It is broadly applicable across various substrates and is supported by comprehensive mechanistic insights from regular photophysical experiments.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":4.4000,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401040","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
The Perylene diimide (PDI) is an underexplored synthetic organic dye with significant potential in photoredox catalysis. We have developed a good chemo- and regioselective, atom-economical methodology for synthesizing trifluoroethylated saturated heterocyclic derivatives and trifluoroethyl-containing cyclobutane derivatives. This process involves the generation of trifluoromethyl radical from the Langlois (CF<sub>3</sub>SO<sub>2</sub>Na) reagent under photoredox conditions, which selectively reacts with the electron-rich terminal double/triple bonds in the diene/enyne framework. The resulting intermediate undergoes a cascade cyclization, yielding the desired compounds in a redox-neutral manner. Our methodology operates under very mild conditions, eliminating the need for transition metals and external oxidizing agents. It is broadly applicable across various substrates and is supported by comprehensive mechanistic insights from regular photophysical experiments.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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