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¹H NMR Chemical Shift Equivalence: Homotopic and Heterotopic Protons01:03

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Shape-Conserving Atom Replacements.

Mikus Puriņš1, Cecile Elgindy1, Mark D Levin1

  • 1Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.

Chemical Reviews
|June 2, 2026
PubMed
Summary
This summary is machine-generated.

Skeletal editing reactions enable atom replacement in molecules, accelerating molecular optimization for drug discovery. This review categorizes these reactions and discusses strategies for shape-conserving transformations.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Recent advances allow precise atom replacement within molecular structures.
  • Skeletal editing reactions are crucial for molecular optimization.
  • These reactions mirror structure-activity-relationship (SAR) study tactics.

Purpose of the Study:

  • To introduce a framework for categorizing atom replacement reactions in aromatic systems.
  • To delineate strategies enabling these transformations.
  • To discuss heuristics for shape-conservation in skeletal editing.

Main Methods:

  • Categorization of atom replacement reactions.
  • Analysis of strategies for skeletal transformations.
  • Discussion of shape-conservation principles (skeletal rotation, vestigial substituents, retrosynthetic simplicity).

Main Results:

  • A comprehensive framework for classifying atom replacement reactions is presented.
  • Strategies for executing shape-conserving skeletal edits are delineated.
  • Examples of C-to-N replacement (e.g., benzene to pyridine) and other aromatic/aliphatic replacements are analyzed.

Conclusions:

  • Skeletal editing reactions offer powerful tools for accelerating discovery chemistry.
  • Understanding shape-conservation heuristics is key for effective molecular design.
  • This review provides a guide to atom replacement strategies in organic synthesis.