Visible-Light Photoredox-Catalyzed Alkylation/1,2-Aryl Migration of Allylic Alcohols with Malonic Esters Leading to δ-Keto Esters
Zhuoming Ma, Huanhuan Cui, Wei Wu, Huilan Yue, Yimou Gong, Zi Yang, Zuli Wang, Dong Yi
Abstract
A visible-light photoredox-catalyzed strategy has been developed for the synthesis of δ-keto esters through alkylation/1,2-aryl migration of allylic alcohols with malonic esters. This transformation could be undergone at room temperature in a step- and atom-economic manner by using Eosin Y and air as a metal-free photocatalyst and green oxidant, respectively. Preliminary mechanistic analysis suggested that 1,2-aryl migration proceeded through a radical process.
Topics & Concepts
Allylic rearrangementChemistryMalonic acidOrganic chemistryAlcoholChemical transformationDecarboxylationTransformation (genetics)CatalysisMedicinal chemistryAliphatic compoundRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis