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Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping
Yan-Bo Li1, Fu-Peng Wu1, Jasper L Tyler1
1Organisch-Chemisches Institut, Universität Münster, Münster, Germany.
Nature Communications
|July 25, 2026
Summary
This study introduces a novel boron-to-carbon single-atom exchange method for aromatic systems. This synthetic strategy precisely modifies molecular structures, enabling detailed structure-function relationship studies.
Area of Science:
- Organic Synthesis
- Medicinal Chemistry
Background:
- Achieving single-atom exchange in aromatic scaffolds while maintaining peripheral substituents is a significant synthetic challenge.
- Existing methods for single-atom skeletal editing in aromatic systems are limited, hindering precise molecular modifications.
Purpose of the Study:
- To develop a novel, single-step methodology for boron-to-carbon atom exchange in aromatic systems.
- To enable the precise modification of molecular frameworks for structure-function relationship studies.
Main Methods:
- A boron-to-carbon swapping reaction was developed using a substituent-rebound process.
- 1,2-Benzazaborines were converted into quinolines using glyoxylic acid as the carbon source.
Main Results:
- The developed method achieves true single-atom skeletal editing by recapturing the original substituent.
- The transformation demonstrates high functional group tolerance.
- The reaction is applicable to late-stage modifications of natural products and pharmaceutical derivatives.
Conclusions:
- This work presents a rare and efficient method for single-atom skeletal editing in aromatic compounds.
- The findings provide a foundation for developing new synthetic manifolds for atom-level precision in molecular design.
- This approach facilitates the detailed investigation of structure-function relationships.
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