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Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide

Xin‐Qian Liu, Yang Guo, Wen-Qin Yu, Biquan Xiong, Peng‐Fei Huang, Kewen Tang, Yu Liu

2023The Journal of Organic Chemistry27 citationsDOI

Abstract

A visible-light-induced three-component reaction of 2-aryl indoles/benzimidazoles, Hantzsch esters, and sodium pyrosulfite through a radical cascade cyclization process with the insertion of sulfur dioxide is described. It provides a novel and powerful way for the synthesis of alkylsulfonated isoquinolinones. Hantzsch esters and Na 2 S 2 O 5 are employed as alkyl radical precursors and SO 2 surrogate, respectively. This transformation exhibits good functional group tolerance and substrate applicability under mild conditions.

Topics & Concepts

ChemistryAlkylArylSulfur dioxideSubstrate (aquarium)SulfurAryl radicalFunctional groupCombinatorial chemistryOrganic chemistryPolymerOceanographyGeologySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Visible-Light-Induced Synthesis of Alkylsulfonated Isoquinolinones from 2-Aryl Indoles/Benzimidazoles through Insertion of Sulfur Dioxide | Litcius