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电化学氧化CF自由基引发的末端和内烯烃的内酯化和醚化反应。

Electrochemical oxidative CF radical-induced lactonization and etherification of terminal and internal alkenes.

作者信息

Grigolato Riccardo, Fantoni Tommaso, Autuori Giuseppe, Lattanzi Matteo, Ferrazzano Lucia, Cabri Walter, Tolomelli Alessandra

机构信息

Tolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry "Giacomo Ciamician", University of Bologna Via Gobetti 85-40129 Bologna Italy

出版信息

RSC Adv. 2025 May 9;15(19):15302-15309. doi: 10.1039/d5ra01852h. eCollection 2025 May 6.

Abstract

Introducing trifluoromethyl (CF) groups enhances drug candidates' properties, improving metabolic stability and bioavailability. This study reports the electrochemical oxidation of Langlois' reagent for CF radical-promoted cyclization, synthesizing functionalized lactones and cyclic ethers from terminal and internal alkenes with good to high yields. Mechanistic insights were supported by cyclic voltammetry, radical scavenger experiments, and DFT calculations. The protocol's efficiency highlights its potential in medicinal chemistry for developing pharmacologically valuable compounds avoiding the use of rare metal electrodes.

摘要

引入三氟甲基(CF)基团可增强候选药物的性质,提高代谢稳定性和生物利用度。本研究报道了Langlois试剂的电化学氧化用于CF自由基促进的环化反应,可从末端烯烃和内烯烃合成功能化内酯和环醚,产率良好至高。循环伏安法、自由基清除剂实验和密度泛函理论(DFT)计算支持了机理研究。该方法的效率突出了其在药物化学中开发具有药理价值化合物的潜力,避免了使用稀有金属电极。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e067/12063074/e38b372a7e11/d5ra01852h-f1.jpg

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