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

Abstract

Comprehensive SummaryA novel electrochemical multicomponent cascade reaction of indole‐tethered alkenes with CF3SO2Na and n‐Bu4NI 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 CF3SO2Na, 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.

Visible-Light-Triggered Difluoroacetylation/Cyclization of Chromone-Tethered Alkenes Enabling Synthesis of Tetrahydroxanthones

“…Based on the above experimental results and the related previous reports, ,− a possible mechanism for this visible light-induced reaction is proposed in Scheme . In the presence of different photocatalysts, the reaction with bromodifluoroacetate or bromodifluoroacetamides as coupling partners proceeds via different pathways.…”

“…Aiming to gain new and flexible methods for the formation of polyfunctionalized tetrahydroxanthones and based on our continuous interest in heteroarene-tethered alkenes, we designed a new series of chromone-tethered alkenes and envision that the reaction of these chromone derivatives under suitable conditions could provide a new access to tetrahydroxanthones. Herein, we report our design of a novel series of chromone-tethered alkenes and the development of a photocatalytic cascade difluoroacetylation-triggered cyclization reaction with bromodifluoroacetamides or bromodifluoroacetates as coupling partners.…”