Nickel-Catalyzed Carbonylation of Cyclopropanol with Benzyl Bromide for Multisubstituted Cyclopentenone Synthesis
Liting Hou, Wenyi Huang, Xianqing Wu, Jingping Qü, Yifeng Chen
Abstract
Herein, we reported a Ni-catalyzed carbonylation of cyclopropanol with benzyl bromide to afford multisubstituted cyclopentenone under 1 atm of CO. The reaction proceeds through cascade carbonylation of benzyl bromides, followed by generation of nickel homoenolate from cyclopropanols via β-C elimination to afford 1,4-diketones, which undergoes intramolecular Aldol condensation to furnish highly substituted cyclopentenone derivatives in moderate to good yields. The reaction exhibits high functional group tolerance with broad substrate scope.
Topics & Concepts
CyclopentenoneChemistryCarbonylationCatalysisIntramolecular forceAldol condensationBromideAldol reactionOrganic chemistryCombinatorial chemistryNickelSubstrate (aquarium)Medicinal chemistryCarbon monoxideGeologyOceanographyAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods