Issue 45, 2019

Merging hypervalent iodine and sulfoximine chemistry: a new electrophilic trifluoromethylation reagent

Abstract

Electrophilic trifluoromethylation is at the forefront of methodologies available for the installation of the CF3 moiety to organic molecules; research in this field is largely spurred by the availability of stable and accessible trifluoromethylation reagents, of which hypervalent iodine and sulfoximine based compounds have emerged as two prominent reagent classes. Herein, we describe the facile synthesis of an electrophilic trifluoromethylation reagent which merges these two scaffolds in a novel hypervalent iodosulfoximine compound. This presents the first analogue of the well-known Togni reagents which neither compromises stability or reactivity. The electronic and physical properties of this new compound were fully explored by X-ray crystallography, cyclic voltammetry, TGA/DSC and DFT analysis. This solution stable, crystalline reagent was found to be competent in the electrophilic trifluoromethylation of a variety of nucleophiles as well as a source of the trifluoromethyl radical. Furthermore, the possibility of enantioinductive transformations could be probed with the isolation of the first enantiopure hypervalent iodine compound bearing a CF3 group, thus this new reagent scaffold offers the opportunity of structurally diversifying the reagent towards asymmetric synthesis.

Graphical abstract: Merging hypervalent iodine and sulfoximine chemistry: a new electrophilic trifluoromethylation reagent

Supplementary files

Article information

Article type
Edge Article
Submitted
25 ágú. 2019
Accepted
20 sep. 2019
First published
27 sep. 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 10516-10523

Merging hypervalent iodine and sulfoximine chemistry: a new electrophilic trifluoromethylation reagent

J. Kalim, T. Duhail, T. Le, N. Vanthuyne, E. Anselmi, A. Togni and E. Magnier, Chem. Sci., 2019, 10, 10516 DOI: 10.1039/C9SC04289J

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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