Photoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation
Jiayi Gu, Wei Zhang, Seth R. Jackson, Yan‐Hong He, Zhi Guan
Abstract
We herein report the photoinduced intermolecular umpolung addition of aromatic ketones/aldehydes with α,β-unsaturated esters via ketyl radical intermediates. Following an intramolecular transesterification, a variety of γ-lactone derivatives are readily accessed. Mechanistic investigations demonstrate the significant role of Hantzsch ester, which serves both as the electron and proton donor.
Topics & Concepts
UmpolungKetylChemistryIntramolecular forceLactoneIntermolecular forceTransesterificationOrganic chemistryRadicalMoleculeCatalysisNucleophileRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods