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Alexandra Doussot¹, Marie-France Bakaï², Eric Fouquet¹

¹Institut des Sciences Moléculaires (ISM), UMR 5255, Univ. Bordeaux, CNRS, Bordeaux INP, 351 Cours de la Libération, 33405 Talence Cedex, France.

Organic Letters

|June 5, 2023

Summary

Researchers generated labeled oxygen molecules (18O2 and 17O2) from endoperoxides for substrate oxidation. This cost-effective method achieved high isotopic enrichment in various products, aiding mechanistic studies.

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Area of Science:

Organic Chemistry
Isotope Chemistry
Chemical Synthesis

Background:

Isotopically labeled oxygen (18O2, 17O2) is crucial for mechanistic studies in organic chemistry.
Existing methods for generating labeled oxygen can be expensive or inefficient.

Purpose of the Study:

To develop a cost-effective and efficient method for generating near-stoichiometric amounts of 18O2 and 17O2 ex situ.
To utilize the generated labeled oxygen for the oxidation of various substrates and investigate reaction mechanisms.

Main Methods:

Generation of 18O2 and 17O2 from endoperoxides in a two-chamber glassware setup.
Oxidation of diverse organic substrates using the generated labeled oxygen species.
Characterization of products using mass spectrometry and 17O Nuclear Magnetic Resonance (NMR) spectroscopy.

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Main Results:

Successful oxidation of various substrates yielding labeled endoperoxides, quinones, phenols, and artemisinin derivatives.
Moderate to good product yields achieved.
High isotopic enrichments (up to 84%) demonstrated for the labeled products.
Cost-effective synthesis demonstrated.

Conclusions:

The developed method provides an affordable and efficient route to access isotopically labeled oxygen for synthetic applications.
The use of labeled oxygen facilitates detailed mechanistic investigations of oxidation reactions.
This approach offers valuable insights into chemical mechanisms through advanced analytical techniques like mass spectrometry and 17O NMR.