Dioxiranes: a half-century journey

Tarek H. El-Assaad, Jayden Zhu, Anjitha Sebastian, Dominic V. McGrath, Ishita Neogi, Keshaba N. Parida

Research output: Contribution to journalReview articlepeer-review

9 Scopus citations

Abstract

Dioxiranes are multi-tasking reagents with mild and selective oxygen transfer attributes. These oxidants are accessed from the reaction of ketones with an oxidant and are employed stoichiometrically or catalytically (in situ) for numerous transformations such as oxidations, epoxidations, C-H hydroxylation, etc. The oxidations involve a broad spectrum of substrates such as alcohols, amines, phenols, silanes, phosphines, etc. Similarly, the epoxidation of olefins, alkynes, allenes and arenes is achieved efficiently, where alkene epoxidation can be regioselective, chemoselective, stereoselective, and stereospecific. Furthermore, C-H hydroxylation using dioxiranes proceeds in both an inter- and intramolecular fashion producing a variety of potent molecules that are difficult to access using other means. Dioxiranes are used for the synthesis of various natural products, drugs, and biomolecules. This review covers all the aforementioned aspects of dioxirane chemistry along with the historical development, characteristics, and reaction mechanisms of dioxirane-mediated transformations established over the last five decades.

Original languageEnglish (US)
Pages (from-to)5675-5725
Number of pages51
JournalOrganic Chemistry Frontiers
Volume9
Issue number20
DOIs
StatePublished - Aug 15 2022
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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