Modular Synthesis of 9,10-Dihydroacridines through an ortho-C Alkenylation/Hydroarylation Sequence between Anilines and Aryl Alkynes in Hexafluoroisopropanol - Organométalliques : Matériaux et Catalyse Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2021

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

Résumé

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.

Domaines

Chimie
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Dates et versions

hal-03245060 , version 1 (15-10-2021)

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Citer

Shengdong Wang, Guillaume Force, Jean-François Carpentier, Yann Sarazin, Christophe Bour, et al.. Modular Synthesis of 9,10-Dihydroacridines through an ortho-C Alkenylation/Hydroarylation Sequence between Anilines and Aryl Alkynes in Hexafluoroisopropanol. Organic Letters, 2021, 23 (7), pp.2565-2570. ⟨10.1021/acs.orglett.1c00487⟩. ⟨hal-03245060⟩
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