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 juin 2022
Accepted
14 août 2022
First published
15 août 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements