“On Water” Palladium Catalyzed Direct Arylation of 1H-Indazole and 1H-7-Azaindazole
Khadija Gambouz, Abdelmoula El Abbouchi, Sarah Nassiri, Franck Suzenet, Mostapha Bousmina, Mohamed Akssira, Gérald Guillaumet, Saı̈d El Kazzouli
Abstract
The C3 direct arylation of 1H-indazole and 1H-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1H-indazoles and C3-aryled 1H-7-azaindazoles via a C3 direct arylation using water as solvent. On water, PPh3 was effective as a ligand along with a lower charge of the catalyst Pd(OAc)2 (5 mol%) at 100 °C, leading to C3-aryled 1H-indazoles or C3-aryled 1H-7-azaindazoles in moderate to good yields.
Topics & Concepts
IndazoleCatalysisPalladiumChemistryReactivity (psychology)Ligand (biochemistry)SolventCombinatorial chemistryMedicinal chemistryOrganic chemistryReceptorBiochemistryMedicineAlternative medicinePathologyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsNanomaterials for catalytic reactions