Synthesis of Aromatic N-Oxides Using Electrochemically Generated Peroxodicarbonate

Area of Science:

• Sustainable chemistry
• Electrochemistry
• Organic synthesis

Background:

• Peroxodicarbonate (PODIC) is an electrochemically generated green oxidizer.
• PODIC offers a sustainable alternative for N-oxidation reactions.
• It avoids hazards associated with concentrated hydrogen peroxide.

Purpose of the Study:

• To develop an efficient and sustainable method for N-oxidation of various nitrogen-containing compounds.
• To explore the utility of electrochemically generated oxidizers in organic synthesis.
• To optimize the N-oxidation reaction using phenoyloxy succinimide (POSI).

Main Methods:

• Electrochemical generation of peroxodicarbonate (PODIC).
• N-oxidation of quinolines, pyridines, and complex tertiary amines using PODIC.
• Employing phenoyloxy succinimide (POSI) as a key reagent.

Main Results:

• Successful N-oxidation of 28 different substrates including quinolines, pyridines, and tertiary amines.
• Isolated yields of N-oxides up to 98% were achieved.
• Demonstrated the efficiency and broad applicability of the POSI-mediated N-oxidation.

Conclusions:

• The developed method provides an efficient and green route for N-oxide synthesis.
• Phenoyloxy succinimide (POSI) is crucial for high yields in N-oxidation.
• This approach aligns with sustainable chemistry principles and offers an alternative to traditional methods.