Photoinduced Oxygen Transfer Using Nitroarenes for the Anaerobic Cleavage of Alkenes

Dan E. Wise, Emma S. Gogarnoiu, Alana D. Duke, Joshua M. Paolillo, Taylor L. Vacala, Waseem A. Hussain, Marvin Parasram

Research output: Contribution to journalArticlepeer-review


Herein we report the anaerobic cleavage of alkenes into carbonyl compounds using nitroarenes as oxygen transfer reagents under visible light. This approach serves as a safe and practical alternative to mainstream oxidative cleavage protocols, such as ozonolysis and the Lemieux-Johnson reaction. A wide range of alkenes possessing oxidatively sensitive functionalities underwent anaerobic cleavage to generate carbonyl derivatives with high efficiency and regioselectivity. Mechanistic studies support that the transformation occurs via direct photoexcitation of the nitroarene followed by a nonstereospecific radical cycloaddition event with alkenes. This leads to 1,3,2- and 1,4,2-dioxazolidine intermediates that fragment to give the carbonyl products. A combination of radical clock experiments and in situ photoNMR spectroscopy revealed the identities of the key radical species and the putative aryl dioxazolidine intermediates, respectively.

Original languageEnglish (US)
Pages (from-to)15437-15442
Number of pages6
JournalJournal of the American Chemical Society
Issue number34
StatePublished - Aug 31 2022

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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