Thermal Nickel-Catalyzed Carbon–Oxygen Cross-Coupling of (Hetero)aryl Halides with Alcohols Enabled by the Use of a Silane Reductant Approach
Liu Yang, Hai-Juan Jiao, Geyang Song, Yanru Huang, Nan Ji, Dong Xue, Wei He
Abstract
Herein, we disclose a highly efficient thermal Ni-catalyzed C–O cross-coupling of aryl halides with primary and secondary alcohols, without the need for photo- or electrocatalysis. The protocol is simple and has a wide substrate scope, particularly for challenging electron-rich aryl halides. Additionally, this methodology has been successfully applied to the late-stage functionalization of drugs and natural products, as well as the synthesis of pharmaceuticals such as pramoxine and the delamanid key intermediate. Preliminary mechanistic studies suggest the in situ generation of active Ni(I) species from inexpensive NiBr 2 -bipyridine and PhSiH 3 .
Topics & Concepts
ArylCatalysisHalideChemistryNickelCombinatorial chemistryElectrocatalystSubstrate (aquarium)Carbon fibersSilaneOrganic chemistryMaterials scienceAlkylElectrochemistryComposite numberElectrodeGeologyPhysical chemistryComposite materialOceanographyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions