Iron-Catalyzed Ortho C–H Homoallylation of Aromatic Ketones with Methylenecyclopropanes
Naoki Kimura, Shiori Katta, Yoichi Kitazawa, Takuya Kochi, Fumitoshi Kakiuchi
Abstract
We report here a C–H homoallylation reaction of aromatic ketones with methylenecyclopropanes (MCPs) only using a catalytic amount of Fe(PMe3)4. A variety of aromatic ketones and MCPs are applicable to the reaction to form ortho-homoallylated aromatic ketones selectively via regioselective scission of the three-membered rings. The homoallylated products are amenable to further elaborations, providing functionalized 1,2-dihydronaphthalenes.
Topics & Concepts
ChemistryRegioselectivityCatalysisAromaticityKetoneMedicinal chemistryReaction conditionsRing (chemistry)Organic chemistryMoleculeCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions