Palladium/Norbornene Cooperative-Catalyzed Cascade Decarboxylative Cyclization of 4-Iodoisoquinolin-1(2<i>H</i>)-ones with <i>o</i>-Bromobenzoic Acids: Access to Diverse Fused Phenanthridinones and Hepta[1,2-<i>c</i>]isoquinolinones
Xiao‐Hong Huang, Caiyun Yang, Fenglin Liu, Xia Li, Bo Liu, Jun‐Feng Kou, Guoli Huang, Ming‐Yu Teng
Abstract
A novel three-component Pd/norbornene cooperative catalysis cascade decarboxylative [2+2+2]/[2+2+3]cyclization of 4-iodoisoquinolin-1(2 H )-ones and o -bromobenzoic acids or 8-bromo-1-naphthoic acid has been developed. The method affords a range of fused phenanthridinones and hepta[1,2- c ]isoquinolinones and displays unique regioselectivity and broad substrate scope. Palladium/norbornene (Pd/NBE)-catalyzed C–H activation and subsequent decarboxylative coupling reactions were involved, and NBE acts as a building block for the construction of rigid nonplanar molecular architectures.
Topics & Concepts
NorborneneChemistryPalladiumCatalysisCascadeRegioselectivityCombinatorial chemistrySubstrate (aquarium)StereochemistryDecarboxylationMedicinal chemistryOrganic chemistryCopolymerOceanographyGeologyPolymerChromatographyCatalytic C–H Functionalization MethodsSynthesis and Biological ActivityCatalytic Alkyne Reactions