Electrochemical or Photoredox Activation of Latent Electrophiles: Three-Component Mumm Rearrangement Cascade Reactions from Alkoxyamines

This report exploits either electrochemical or photoredox triggers to promote the oxidative mesolytic cleavage of alkoxyamines to establish multicomponent Mumm rearrangement cascade reactions for the synthesis of imides and imidates. Readily accessible, bench-, air-, and moisture-stable alkoxyamines derived from 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) serve as masked carbocations in this approach.

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Publication Details

Journal
Organic Letters
Published
2026-01-08
DOI
https://doi.org/10.1021/acs.orglett.5c05049
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Electrochemical or Photoredox Activation of Latent Electrophiles: Three-Component Mumm Rearrangement Cascade Reactions from Alkoxyamines

Alex C. Bissember, Michelle L. Coote, Tan N. Huynh, Philip L. Norcott
Organic Letters
Radical Photochemical Reactions
article

Electrochemical or Photoredox Activation of Latent Electrophiles: Three-Component Mumm Rearrangement Cascade Reactions from Alkoxyamines

Alex C. Bissember, Michelle L. Coote, Tan N. Huynh, Philip L. Norcott
article en

Abstract

This report exploits either electrochemical or photoredox triggers to promote the oxidative mesolytic cleavage of alkoxyamines to establish multicomponent Mumm rearrangement cascade reactions for the synthesis of imides and imidates. Readily accessible, bench-, air-, and moisture-stable alkoxyamines derived from 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) serve as masked carbocations in this approach.

Organic LettersVol. 28(3)
University of Tasmania (AU), Flinders University (AU), Center for Nanoscale Science and Technology (US)
Openalex Percentile: Top 94%
Radical Photochemical Reactions
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