Photocatalytic Decarboxylative [3 + 2] and [4 + 2] Annulation of Enynals and γ,σ-Unsaturated <i>N</i>-(Acyloxy)phthalimides by NaI/PPh<sub>3</sub> Catalysis
Xiaojie Liu, Sheng-Yun Zhou, Yuting Xiao, Qing Sun, Xin Lü, Yang Li, Jin‐Heng Li
Abstract
A practical and eco-friendly strategy for the radical-mediated decarboxylative [3 + 2] and [4 + 2] annulation of enynals and γ,σ-unsaturated N-(acyloxy)phthalimides through the photoactivation of an electron donor–acceptor (EDA) complex has been developed. A wide range of primary, secondary, and tertiary alkyl N-hydroxyphthalimide (NHP) esters can be used as suitable substrates for the synthesis of fused ketones without any transition-metal catalysts or oxidants. This protocol features a broad substrate scope, excellent selectivity, and clean reaction conditions.
Topics & Concepts
PhthalimidesChemistryAnnulationCatalysisPhotocatalysisSubstrate (aquarium)Combinatorial chemistryOrganic chemistryMedicinal chemistryPhthalimideGeologyOceanographyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions