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氟融合:NHC催化的亲核芳香取代反应揭示了功能性全氟二芳基甲酮。

FluoroFusion: NHC-Catalyzed Nucleophilic Aromatic Substitution Reaction Unveils Functional Perfluorinated Diarylmethanones.

作者信息

Chan Cheng-Lin, Lee Shao-Chi, Lin Pei-Shan, Tapales Radyn Vanessa Phaz P, Li Jia-Syuan, Lai Chun-An, Lee Jyh-Tsung, Li Chien-Hung, Liao Hsuan-Hung

机构信息

Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804201, Taiwan (R.O.C.).

Department of International Ph.D. Program for Science, National Sun Yat-sen University, Kaohsiung 804201, Taiwan (R.O.C.).

出版信息

Org Lett. 2024 Mar 22;26(11):2338-2342. doi: 10.1021/acs.orglett.4c00677. Epub 2024 Mar 8.

Abstract

A mild, facile, and metal-free approach via the -heterocyclic carbene-catalyzed SAr reaction between aryl aldehydes with perfluoroarenes to obtain the coveted functional perfluorinated diarylmethanones is disclosed. This method accommodates a diverse substrate range and exhibits notable tolerance toward various functional groups. Our success in modifying biologically relevant molecules, crafting a fully fluorinated bioisosteric analogue of drug candidate , and highlighting the potential of these ketones as valuable electrolyte additives for lithium-ion batteries (LIBs) underscores the versatility of our methodology.

摘要

本文公开了一种温和、简便且无金属的方法,通过-杂环卡宾催化芳醛与全氟芳烃之间的SAr反应来获得令人垂涎的功能性全氟二芳基甲酮。该方法具有广泛的底物范围,并且对各种官能团表现出显著的耐受性。我们在修饰生物相关分子、制备候选药物的全氟生物电子等排体类似物以及突出这些酮作为锂离子电池(LIBs)有价值的电解质添加剂的潜力方面取得的成功,强调了我们方法的多功能性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cc4/10964231/69340d4a6d6a/ol4c00677_0001.jpg

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