In situ formation of the electrophilic phenylselenenyl sulfate triggered by light

Abstract

Ammonium persulfate is a mild oxidant capable of oxidizing the selenium-selenium bond through thermal activation or under drastic acid catalysis. In this paper we highlight that this reaction can be activated photochemically, starting from diphenyl diselenide in the absence of any organic or and/or metallic photocatalyst or additive. The protocol was applied to a well-known panel of selenoalkoxylation reactions and the obtained results clearly indicate the involvement of an electrophilic selenium reagent.

GRAPHICAL ABSTRACT

Keywords:

• Electrophilic selenium
• alkoxyselenenylation
• BlueLed
• persulfate
• diphenyl diselenide

Acknowledgments

University of Perugia is gratefully acknowledged for the financial support “Fondo per la Ricerca di Base 2022”. This work was performed under the umbrella of the international Scientific Network SeSRedCat (Selenium Sulphur and Redox Catalysts). The authors thank Dr. K. Indira Priyadarsini, PhD, FRSC, FNASc DAE Raja Ramanna Fellow, UM-DAE Centre for Excellence in Basic Sciences, University of Mumbai, and Dr. Dr. Beena G. Singh, Scientific Officer-F Radiation & Photochemistry Division, Bhabha Atomic Research Centre (India), for the fruitful discussion about the plausible mechanism.

Disclosure statement

No potential conflict of interest was reported by the authors.