Issue 26, 2019

Late stage functionalization of heterocycles using hypervalent iodine(iii) reagents

Abstract

Late stage functionalization (LSF) through direct X–H manipulations (X = C, N) enables synthetic chemists to accelerate the diversification of natural products, agrochemicals and pharmaceuticals allowing rapid access to novel bioactive molecules without resorting to arduous de novo synthesis. LSF does not only allow tapping of the hitherto unexplored chemical space but also renders the synthetic sequence more straightforward, atom economical and cost-effective. In this regard, the recent decade has witnessed the emergence of hypervalent iodine(III) reagents as a powerful synthetic tool owing to their easy availability, mild reaction conditions, remarkable oxidizing properties and high functional group tolerance. Iodine(III) reagents have tremendous applications in the regio- and chemo-selective late-stage functionalization of a diverse variety of heterocycles through an exciting range of transformations, such as oxidative amination, cross-dehydrogenative coupling (CDC), fluoroalkylation, azidation, halogenation and oxidation. The present review, classified according to the types of synthetic methods involved, encompasses all these recent developments in the field of transition-metal-free iodine(III)-catalyzed/mediated direct functionalizations of heterocycles with representative examples and insightful mechanistic discussions.

Graphical abstract: Late stage functionalization of heterocycles using hypervalent iodine(iii) reagents

Article information

Article type
Review Article
Submitted
25 မတ် 2019
Accepted
10 ဇွန် 2019
First published
10 ဇွန် 2019

Org. Biomol. Chem., 2019,17, 6326-6341

Late stage functionalization of heterocycles using hypervalent iodine(III) reagents

R. Budhwan, S. Yadav and S. Murarka, Org. Biomol. Chem., 2019, 17, 6326 DOI: 10.1039/C9OB00694J

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