Palladium-Catalyzed Regioselective Monofluoroallylation of Indoles with <i>gem</i>-Difluorocyclopropanes
Zhenjie Wang, Chuang Liu, Junhai Huang, Liliang Huang, Huangdi Feng
Abstract
We present a palladium-catalyzed ring-opening reaction that induces indoles to cross-couple with gem -difluorocyclopropanes. The reaction proceeds through a domino process of C–C bond activation and C–F bond elimination, followed by C–C(sp2) coupling to produce various 2-fluoroallylindoles. This method is characterized by its high functional group tolerance, good yields and high regioselectivity, under base-free conditions. The synthetic utility of the products is illustrated by the functionalization of the NH and C2 positions of the indole scaffold.
Topics & Concepts
RegioselectivityChemistryIndole testPalladiumCatalysisFunctional groupRing (chemistry)Combinatorial chemistryDominoSurface modificationCoupling reactionMedicinal chemistryStereochemistryOrganic chemistryPhysical chemistryPolymerFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods