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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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Introduction
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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2,3-Diaryl Indanone Construction via the Neophyl Rearrangement.

Zhikun Wu1, Lingzhi Hu1, Shunxi Dong1

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Organic Letters
|April 21, 2026
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Summary
This summary is machine-generated.

Researchers developed a new method for the neophyl rearrangement using unactivated C(sp3)-H bonds. This reaction efficiently synthesizes 2,3-diaryl indanone derivatives, important structures in medicinal chemistry.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • The neophyl rearrangement is a known radical migration reaction.
  • Direct functionalization of unactivated C(sp3)-H bonds is challenging.

Purpose of the Study:

  • To develop a novel method for the formal 2,3-difunctionalization of 3,3-disubstituted indanones.
  • To construct 2,3-diaryl indanone derivatives, a privileged scaffold in bioactive molecules.

Main Methods:

  • Utilized a hypervalent iodine reagent and a catalytic chiral scandium complex.
  • Employed alcohols or water as nucleophiles.

Main Results:

  • Achieved efficient synthesis of 2,3-diaryl indanone derivatives.
  • Obtained products in excellent yields with high diastereoselectivity.
  • Rationalized radical generation via single-electron transfer and deprotonation, followed by ligand coupling.

Conclusions:

  • The developed method provides a rare example of neophyl rearrangement from unactivated C(sp3)-H bonds.
  • This reaction is effective for synthesizing valuable bioactive scaffolds.
  • The process involves a novel iodine(III) intermediate.