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February 8, 2026Angewandte Chemie

Millisecond Aliphatic Iodonium‐Claisen Rearrangement Enabling Dual Functionalization of Alkenyl Iodanes

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Authors

XHXin HuangJJJiangtao JiBLBingjie Liu

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Overview

Demonstrates rapid dual functionalization of alkenyl iodanes using iodonium Claisen rearrangement, indicating new synthetic pathways.

Key Points

  • This research aims to explore a rapid iodonium Claisen rearrangement for functionalizing alkenyl iodanes.
  • Conducted aliphatic iodonium Claisen rearrangements at −78 °C.
  • Utilized a variety of nucleophiles including allyl silanes and stannyl nitriles.
  • Investigated the mechanistic details of rapid reaction kinetics.
  • Achieved rearrangement completion in less than 0.1 seconds.
  • Expanded substrate scope and product diversity through new nucleophile interactions.
  • Mechanistic studies confirmed a significant influence of hypervalent iodine on reaction speed and selectivity.

Cite This Study

Huang et al. (2026) studied this question.

synapsesocial.com/papers/698828410fc35cd7a8847a17https://doi.org/10.1002/ange.202526108
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Also Consider

Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

  1. 1Outside Back Cover: Millisecond Aliphatic Iodonium‐Claisen Rearrangement Enabling Dual Functionalization of Alkenyl Iodanes2026
  2. 2Aminohalogenation of Alkenes Enabled by I(I)/I(III) Catalysis2026
  3. 3Reductive <i>ortho</i>-Cyanomethylation of Aryl Iodanes with MeCN via One-pot Iodonium-Claisen Rearrangement2025
  4. 4Kinetic, Spectroscopic, and Computational Investigation of Oxidative Aminative Alkene Cleavage Reveals an N-Iodonium-Iminoiodinane Pathway2025
  5. 5Diversity-Oriented Synthesis of 3-Iodochromones and Heteroatom Analogues via ICl-Induced Cyclization2006 · 159 citations