Versatile New Reagent for Nitrosation under Mild Conditions
Jordan D Galloway1, Cristian Sarabia1, James C Fettinger2
1Department of Chemistry and Chemical Biology, University of California, Merced, Merced, California 95343, United States.
Organic Letters
|April 12, 2021
Summary
A novel chemical reagent enables efficient transnitrosation under mild conditions. This stable reagent offers high functional group tolerance, accessing challenging nitroso compounds previously unavailable.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Traditional nitrosation methods often require harsh conditions.
- Many substrates are sensitive to oxidation or reversible transnitrosation.
Purpose of the Study:
- To develop a new chemical reagent for mild and efficient transnitrosation.
- To synthesize challenging nitroso compounds and their isotopologues.
Main Methods:
- Development of a novel, air- and moisture-stable transnitrosation reagent.
- Application of the reagent across various solvents and functional group tolerant substrates.
- Characterization of synthesized nitroso compounds, including 15N isotopologues.
- X-ray crystallography and computational analysis of reagent isomers.
Main Results:
- The new reagent facilitates transnitrosation under mild experimental conditions.
- High functional group tolerance was observed, even for sensitive substrates.
- Several challenging nitroso compounds, including 15N isotopologues, were synthesized for the first time.
- Two stable rotational isomers of the reagent were identified, with one isomer being catalytically active.
Conclusions:
- A versatile and stable reagent for transnitrosation has been developed.
- This reagent expands the scope of accessible nitroso compounds.
- Understanding of reagent isomerism and reactivity provides insights for future reagent design.
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