Issue 1, 2022

Direct radical functionalization methods to access substituted adamantanes and diamondoids

Abstract

Adamantane derivatives have diverse applications in the fields of medicinal chemistry, catalyst development and nanomaterials, owing to their unique structural, biological and stimulus-responsive properties, among others. The synthesis of substituted adamantanes and substituted higher diamondoids is frequently achieved via carbocation or radical intermediates that have unique stability and reactivity when compared to simple hydrocarbon derivatives. In this review, we discuss the wide range of radical-based functionalization reactions that directly convert diamondoid C–H bonds to C–C bonds, providing a variety of products incorporating diverse functional groups (alkenes, alkynes, arenes, carbonyl groups, etc.). Recent advances in the area of selective C–H functionalization are highlighted with an emphasis on the H-atom abstracting species and their ability to activate the particularly strong C–H bonds that are characteristic of these caged hydrocarbons, providing insights that can be applied to the C–H functionalization of other substrate classes.

Graphical abstract: Direct radical functionalization methods to access substituted adamantanes and diamondoids

Article information

Article type
Review Article
Submitted
12 Aug 2021
Accepted
08 Oct 2021
First published
09 Oct 2021

Org. Biomol. Chem., 2022,20, 10-36

Direct radical functionalization methods to access substituted adamantanes and diamondoids

W. K. Weigel, H. T. Dang, A. Feceu and D. B. C. Martin, Org. Biomol. Chem., 2022, 20, 10 DOI: 10.1039/D1OB01916C

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