Synthesis of Cyclopentenones through Rhodium-Catalyzed C–H Annulation of Acrylic Acids with Formaldehyde and Malonates
Shuling Yu, Chao Hong, Zhanxiang Liu, Yuhong Zhang
Abstract
An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C–H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.
Topics & Concepts
ChemistryFormaldehydeMalonateRhodiumCatalysisAlkylationOrganic chemistryHalideAnnulationAlkylAcrylic acidCopolymerPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms