Palladium-Catalyzed Reductive Aminocarbonylation of <i>o</i>-Iodophenol-Derived Allyl Ethers with <i>o</i>-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1<i>H</i>)-ones
Jianli Liu, Wei Wang, Xinxin Qi, Xiao‐Feng Wu
Abstract
An attractive palladium-catalyzed reductive aminocarbonylation reaction of allylic ethers has been explored for the synthesis of 3-alkenylquinolin-2(1H)-one derivatives. With Mo(CO)6 as both CO surrogate and reductant, a variety of 3-alkenylquinolin-2(1H)-ones were obtained in good to excellent yields from o-iodophenol-derived allyl ethers with o-nitrobenzaldehydes as the nitrogen sources. This reaction proceeds through a cascade pathway and does not rely on high-pressure CO gas as needed in former allylic carbonylation reactions. This strategy provides a new pathway for the construction of 3-alkenylquinolin-2(1H)-ones.
Topics & Concepts
ChemistryAllylic rearrangementCarbonylationPalladiumCatalysisMedicinal chemistryOrganic chemistryCombinatorial chemistryCarbon monoxideCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis