Issue 20, 2022

Dioxiranes: a half-century journey

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.

Graphical abstract: Dioxiranes: a half-century journey

Article information

Article type
Review Article
Submitted
22 jun 2022
Accepted
14 aug 2022
First published
15 aug 2022

Org. Chem. Front., 2022,9, 5675-5725

Dioxiranes: a half-century journey

T. H. El-Assaad, J. Zhu, A. Sebastian, D. V. McGrath, I. Neogi and K. N. Parida, Org. Chem. Front., 2022, 9, 5675 DOI: 10.1039/D2QO01005D

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