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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.

DOI:10.1021/acs.orglett.4c00677
PMID:38458971
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10964231/
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/d12d517f1c4c/ol4c00677_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cc4/10964231/69340d4a6d6a/ol4c00677_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cc4/10964231/93a937913180/ol4c00677_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cc4/10964231/d12d517f1c4c/ol4c00677_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cc4/10964231/69340d4a6d6a/ol4c00677_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cc4/10964231/93a937913180/ol4c00677_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5cc4/10964231/d12d517f1c4c/ol4c00677_0003.jpg

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本文引用的文献

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A protocol for the gram-scale synthesis of polyfluoroaryl sulfides via an SAr step.通过 SAr 步骤实现聚氟芳基硫醚的克级规模合成的方案。
STAR Protoc. 2023 Mar 17;4(1):102043. doi: 10.1016/j.xpro.2023.102043. Epub 2023 Jan 19.
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Transition-Metal-Free Synthesis of Polyfluoro-Polyarylmethanes via Direct Cross-Coupling of Polyfluoroarenes and Benzyl Chlorides.
Chemistry. 2023 Apr 3;29(19):e202203427. doi: 10.1002/chem.202203427. Epub 2023 Feb 27.
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Scaffold modified Vemurafenib analogues as highly selective mitogen activated protein kinase kinase 4 (MKK4) inhibitors.支架修饰的威罗非尼类似物作为高选择性丝裂原活化蛋白激酶激酶 4(MKK4)抑制剂。
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Current Contributions of Organofluorine Compounds to the Agrochemical Industry.有机氟化合物对农用化学品行业的当前贡献。
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Fluorinated Aromatic Diluent for High-Performance Lithium Metal Batteries.用于高性能锂金属电池的氟化芳族稀释剂
Angew Chem Int Ed Engl. 2020 Aug 24;59(35):14869-14876. doi: 10.1002/anie.202003663. Epub 2020 Jun 17.
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Entrectinib: First Global Approval.恩曲替尼:全球首次获批。
Drugs. 2019 Sep;79(13):1477-1483. doi: 10.1007/s40265-019-01177-y.
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The biodegradation vs. biotransformation of fluorosubstituted aromatics.含氟取代芳烃的生物降解与生物转化
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Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.氮杂环卡宾催化的有机反应
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