Light Illuminates Polarity-Mismatched Cycloaddition to Convert Isoquinoliniums into Phenylnaphthyl Sulfones
Yunlong Qin, Yuanyuan Zeng, Weihan Wang, Congcong Zhang, Jianing Zhang, Zerong GUO, Yang Zhao, Qilin Wang
Abstract
A visible-light-driven skeletal editing strategy that converts readily available isoquinolinium salts into phenylnaphthyl sulfones via a formal CN-to-CC atom-pair swap is presented. The process is triggered by an isoquinolinium-carbonate electron donor-acceptor (EDA) complex that, upon blue-light excitation, undergoes single-electron transfer to initiate a polarity-mismatched (4 + 2) radical annulation with alkynyl sulfones. The reaction proceeds at room temperature without external photocatalysts, tolerates diverse functional groups (including halides), and furnishes the targeted diarylsulfones with high efficiency.
Topics & Concepts
ChemistryAnnulationCycloadditionSwap (finance)Combinatorial chemistryReaction conditionsProcess (computing)Organic chemistryFunctional groupElectron transferPhotochemistryMoleculeCatalysisSulfoneRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods