Synthesis of Naphtho[1′,2′:4,5]furo[3,2-<i>b</i>]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C–H Functionalization of <i>N</i>-Pyridyl-2-pyridones with Diazonaphthalen-2(1<i>H</i>)-ones
Yuanshuang Xu, Yujing Xiao, Xinying Zhang, Xuesen Fan
Abstract
Presented herein is an unprecedented synthesis of naphtho[1′,2′:4,5]furo[3,2- b ]pyridinones via Ir(III)-catalyzed C6/C5 dual C–H functionalization of N -pyridyl-2-pyridones with diazonaphthalen-2(1 H )-ones. This protocol forms C–C and C–O bonds in one pot in which diazonaphthalen-2(1 H )-ones serve as bifunctional reagents, providing both alkyl and aryloxy sources. To the best of our knowledge, this is the first example of an Ir(III)-catalyzed synthesis of the title compounds by using diazonaphthalen-2(1 H )-ones as bifunctional substrates. Notably, this method features operational simplicity, good functional group tolerance, high efficiency, and high atom economy.
Topics & Concepts
BifunctionalChemistrySurface modificationReagentCatalysisAtom economyAlkylFunctional groupCombinatorial chemistryDual roleMedicinal chemistryStereochemistryOrganic chemistryPhysical chemistryPolymerCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions