Benzodithiazoles‐Sulfoximines: Preparation, Properties and Reactivities as Radical Perfluoroalkylating Agents

We describe the preparation of S‐perfluoroalkyl benzodithiazole trioxides as radical perfluoroalkylating reagents. Their syntheses were performed on a multi‐gram scale by an oxidative cyclization connecting the nitrogen of a sulfoximine and a sulfur atom previously introduced in the ortho position o...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-07, Vol.365 (14), p.2392-2399
Main Authors: Duhail, Thibaut, Messaoudi, Samir, Dagousset, Guillaume, Marrot, Jérôme, André‐Barrès, Christiane, Magnier, Emmanuel, Anselmi, Elsa
Format: Article
Language:English
Subjects:
Chemical Sciences
Fluorine
Organic chemistry
Perfluoro compounds
Photocatalysis
Photoredox catalysis
Radicals
Reactivity
Reagents
Scale (corrosion)
Sulfoximines
Sulfur heterocycles
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We describe the preparation of S‐perfluoroalkyl benzodithiazole trioxides as radical perfluoroalkylating reagents. Their syntheses were performed on a multi‐gram scale by an oxidative cyclization connecting the nitrogen of a sulfoximine and a sulfur atom previously introduced in the ortho position of this group. The structures and properties of these new molecules were carefully examined by X‐Ray diffraction, DFT calculations and cyclic voltammetry. These data clearly highlight the enhanced reactivity of these cyclic sulfoximines compared to their open analogues. This was confirmed by photoredox catalysis experiments that revealed interesting reactivity, most especially for the introduction of di‐ and monofluoroalkyl chains.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300553