Redox-Neutral Cascade Trifluoromethylation of Dienes and Enynes using a Perylene Diimide (PDI) Organophotocatalyst

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-11-05 DOI:10.1002/adsc.202401040
Krishna Gopal Ghosh, Koustav Pal, Manasi Mallick, Debabrata Das, Devarajulu Sureshkumar
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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.
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使用过二亚胺 (PDI) 有机光催化剂进行二烯烃和炔烃的氧化还原中性级联三氟甲基化反应
亚哌二酰亚胺(PDI)是一种尚未充分开发的合成有机染料,在光氧化催化方面具有巨大潜力。我们开发了一种化学和区域选择性好、原子经济的方法,用于合成三氟乙基化饱和杂环衍生物和含三氟乙基的环丁烷衍生物。这一过程包括在光氧化条件下,由 Langlois(CF<sub>3</sub>SO<sub>2</sub>Na)试剂生成三氟甲基自由基,该自由基选择性地与二烯/炔框架中电子丰富的末端双键/三键发生反应。生成的中间体发生级联环化反应,以氧化还原中性的方式生成所需的化合物。我们的方法操作条件非常温和,无需过渡金属和外部氧化剂。它广泛适用于各种底物,并得到了常规光物理实验所提供的全面机理见解的支持。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
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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