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无催化剂条件下硼氢化钠促进全氟芳烃的氢氟去氟化反应

Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH.

机构信息

Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078, United States.

出版信息

Org Lett. 2021 Mar 5;23(5):1588-1593. doi: 10.1021/acs.orglett.0c04305. Epub 2021 Feb 15.

Abstract

Presented is an economical means of removing fluorine from various highly fluorinated arenes using NaBH. The procedure was adapted for different classes of perfluoroarenes. A novel isomer of an emerging class of organic dyes based on the carbazole phthalonitrile motif was succinctly synthesized in two steps from tetrafluorophthalonitrile, demonstrating the utility of the hydrodefluorination procedure. Initial exploration of the dye shows it to be photoactive and capable of facilitating contrathermodynamic styrenoid / isomerization.

摘要

本文提出了一种使用 NaBH 从各种高度氟化的芳烃中去除氟的经济方法。该方法适用于不同类别的全氟芳烃。基于咔唑二腈基的新型有机染料,通过两步法从四氟苯二腈简洁合成,展示了该氢氟化物去除方法的实用性。该染料的初步探索表明其具有光活性,并能够促进反热力学苯乙烯类化合物/异构化。

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本文引用的文献

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Organocatalyzed Fluoride Metathesis.有机催化的氟化物复分解反应
Org Lett. 2020 Dec 4;22(23):9351-9355. doi: 10.1021/acs.orglett.0c03593. Epub 2020 Nov 17.
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Selective Defluoroallylation of Trifluoromethylarenes.三氟甲基芳烃的选择性去全氟烯丙基化反应。
J Am Chem Soc. 2019 Sep 11;141(36):14120-14125. doi: 10.1021/jacs.9b07766. Epub 2019 Aug 28.
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Palladium Catalyzed Hydrodefluorination of Fluoro-(hetero)arenes.钯催化氟(杂)芳烃的加氢脱氟反应
Org Lett. 2019 Apr 5;21(7):2482-2487. doi: 10.1021/acs.orglett.9b00889. Epub 2019 Mar 26.

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