4.8 Article

Modular Synthesis of 9,10-Dihydroacridines through an ortho-C Alkenylation/Hydroarylation Sequence between Anilines and Aryl Alkynes in Hexafluoroisopropanol

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ORGANIC LETTERS
卷 23, 期 7, 页码 2565-2570

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00487

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  1. ANR [ANR-17-CE07-0003, ANR-16-CE07-0022]
  2. CNRS
  3. Ecole Polytechnique
  4. Universite Paris-Saclay
  5. Agence Nationale de la Recherche (ANR) [ANR-16-CE07-0022, ANR-17-CE07-0003] Funding Source: Agence Nationale de la Recherche (ANR)

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A modular one-pot synthesis of 9,10-dihydroacridine frameworks was achieved through a reaction sequence involving selective ortho-C alkenylation of diarylamines with aryl alkynes followed by intramolecular hydroarylation. The combination of hexafluoroisopropanol and triflimide as catalysts played a crucial role in triggering the whole process.
9,10-Dihydroacridines are frequently encountered as key scaffolds in OLEDs. However, accessing those compounds from feedstock precursors typically requires multiple steps. Herein, a modular one-pot synthesis of 9,10-dihydroacridine frameworks is achieved through a reaction sequence featuring a selective ortho-C alkenylation of diarylamines with aryl alkynes followed by an intramolecular hydroarylation of the olefin formed as an intermediate. This transformation was accomplished by virtue of the combination of hexafluoroisopropanol and triflimide as a catalyst that triggers the whole process.

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