Electrochemical Multicomponent Cascade Radical Process Enabling Synthesis of Iodomethyl Spiropyrrolidinyl-Oxindoles

Abstract

A novel electrochemical multicomponent cascade reaction of indole-tethered alkenes with CF ₃SO ₂Na and n-Bu ₄NI has been developed, which enables the rapid assembly of spiropyrrolidinyl-oxindoles in good yields. The experimental results and DFT calculations suggest that this reaction proceeds through the oxidation of CF ₃SO ₂Na, radical coupling with alkene, spirocyclization, oxidation of sulfinate, iodide substitution, and water coupling. This strategy features mild reaction conditions, easy-to-handle reactants, and good chemical yields. This finding not only enriches the research contents of indole-tethered alkenes but also provides a green strategy for the construction of spiropyrrolidinyl-oxindoles compared with the existing methodologies.

Keywords

Spiropyrrolidinyl-oxindoles / Electrosynthesis / Indole-tethered alkenes / CF ₃SO ₂Na / DFT calculation / Multicomponent reaction / Radical reactions / Cross-Coupling / Green chemistry

RIGHTS & PERMISSIONS

2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH