Efficient and Solvent-Free Oxidation Coupling of Amines to Imines Using Persulfate as Oxidant with Ultrasound Assistance

Abstract

The coupling reactions of amines into imines oxidized by persulfate with the assistance of ultrasound were carried out. The reaction conditions were optimized and the effect of ultrasonic was also investigated. The results indicated that Na₂S₂O₈ in combination with ultrasound possessed excellent oxidative performance, which made this transformation smoothly proceed under the conditions of solvent-/catalyst- free, and low reaction temperature, giving excellent yields of imines in short reaction time. Our procedure had high reaction tolerance to various primary benzylic amines, demonstrating good universality. Furthermore, a tentative reaction mechanism and pathway were proposed.

Keywords:

• persulfate
• ultrasonic
• oxidative coupling
• amines
• imines

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Funding

This work was supported by Natural Science Foundation of Shandong Province, China (Grant No. ZR2020KE035) and National Natural Science Foundation of China (Grant No. 21878178).