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分别与亲核或亲电含氟反应伙伴进行无溶剂和无催化剂合成α-二氟代和多氟芳基化化合物

Solvent- and Catalyst-Free Synthesis of -Difluorinated and Polyfluoroarylated Compounds with Nucleophilic or Electrophilic Fluorine-Containing Reaction Partners, Respectively.

作者信息

Li Lingheng, Li Jinshan

机构信息

Department of Photography, Tianjin University of Technology, Tianjin 300384, China.

School of Chemistry and Chemical Engineering, Hainan University, Haikou 570228, China.

出版信息

Molecules. 2024 Feb 2;29(3):697. doi: 10.3390/molecules29030697.

DOI:10.3390/molecules29030697
PMID:38338440
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10856203/
Abstract

A novel, efficient and environmentally friendly solvent-free and catalyst-free approach for the synthesis of structurally diverse -difluorinated and polyfluoroarylated derivatives with readily available nucleophilic and electrophilic fluorine-containing reaction partners, difluoroenoxysilane and pentafluorobenzaldehyde, is described. This neat protocol is induced by the direct hydrogen-bond interactions between fluorinated and non-fluorinated reactants without the use of heavy metal catalysts or volatile organic solvents and with no need for column chromatographic separation for most cases.

摘要

本文描述了一种新颖、高效且环境友好的无溶剂、无催化剂方法,用于合成结构多样的含氟二氟化和多氟芳基化衍生物,反应原料亲核和亲电含氟试剂为易于获得的二氟烯氧基硅烷和五氟苯甲醛。这个简洁的方案是由氟化和非氟化反应物之间的直接氢键相互作用引发的,无需使用重金属催化剂或挥发性有机溶剂,并且在大多数情况下无需柱色谱分离。

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本文引用的文献

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Photoinduced Defluorinative Branch-Selective Olefination of Multifluoro (Hetero)arenes.光诱导脱氟区域选择性烯烃化多氟(杂)芳烃。
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通过 HFIP 催化的水合乙醛与二氟烯氧硅烷的 Mukaiyama 羟醛反应合成 2,2-二氟-3-羟基-1,4-二酮。
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HFIP-catalyzed direct dehydroxydifluoroalkylation of benzylic and allylic alcohols with difluoroenoxysilanes.HFIP 催化的二氟烯基硅烷与苄醇和烯丙醇的直接去羟二氟烷基化反应。
Chem Commun (Camb). 2021 Feb 1;57(8):1050-1053. doi: 10.1039/d0cc06980a.
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Catalytic Enantioselective Synthesis of Difluoromethylated Tetrasubstituted Stereocenters in Isoindolones Enabled by a Multiple-Fluorine System.多氟体系促进的异吲哚酮中手性四取代立体中心的催化对映选择性二氟甲基化合成。
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