Approach to Geminal Bisperoxides from Aldehydes via BR3/O2-Enabled Peroxidation
Terim Seo1, Gyoungho Noh1, Do Hyun Ryu1
1Department of Chemistry, Sungkyunkwan University, Suwon16419, Republic of Korea.
Organic Letters
|July 27, 2026
Summary
A new method uses trialkylborane and oxygen to create geminal bisperoxides from aldehydes. This efficient synthesis yields valuable compounds for further chemical transformations.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Aldehydes are versatile starting materials in organic synthesis.
- Selective synthesis of geminal bisperoxides remains a challenge.
Purpose of the Study:
- To develop a novel method for the selective synthesis of geminal bisperoxides.
- To explore the synthetic utility of the obtained geminal bisperoxides.
Main Methods:
- Trialkylborane/O2-enabled peroxidation of aldehydes.
- Characterization of synthesized geminal bisperoxides.
- Demonstration of synthetic transformations of geminal bisperoxides.
Main Results:
- High yields (up to >99%) of geminal bisperoxides were achieved from simple aldehyde precursors.
- Diverse transformations into azidoperoxides, cyanoperoxides, peroxyesters, esters, and carboxylic acids were demonstrated.
- Mechanistic studies indicated a radical pathway for the peroxidation reaction.
Conclusions:
- The developed trialkylborane/O2-enabled peroxidation offers an efficient route to geminal bisperoxides.
- The synthesized geminal bisperoxides serve as valuable intermediates for accessing a variety of functionalized compounds.
- The reaction proceeds via a radical mechanism, providing insights into the synthetic pathway.
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