Modular Synthesis of 9,10-Dihydroacridines through an <i>ortho</i>-C Alkenylation/Hydroarylation Sequence between Anilines and Aryl Alkynes in Hexafluoroisopropanol
Shengdong Wang, Guillaume Force, Jean‐François Carpentier, Yann Sarazin, Christophe Bour, Vincent Gandon, David Lebœuf
Abstract
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.
Topics & Concepts
ChemistryIntramolecular forceArylOlefin fiberModular designSequence (biology)Combinatorial chemistryCatalysisOrganic chemistryMedicinal chemistryComputer scienceProgramming languageAlkylBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions