Cambridge Open Engage home
What is Cambridge Open Engage?
How to Submit
Browse
About
News [opens in a new tab]

Synthesis of -Tosyloxylated gem-Difluoroalkanes via Oxidative Fluorination of Vinyl Sulfonates Featuring A [2,3]-Sulfonyloxy Migration

15 February 2022, Version 2
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The gem-difluoroalkanes widely exist in pharmaceuticals, agrochemicals and materials. Reported herein is a facile synthesis of tosyloxylated gem-difluoroalkanes via an oxidative fluorination of readily available vinyl sulfonates. An intriguing [2,3]-sulfonyloxy migration is involved as a key step. The OTs group in the product enables a divergent and modular synthesis of a wide variety of functionalized gem-difluoroalkanes via reliable SN2 reactions. Notable features of this protocol include mild reaction conditions, high efficiency and remarkably good functional-group tolerance.

Keywords

gem-difluorination
[2 3]-sulfonyloxy migration
vinyl sulfonate
hypervalent iodine
late-stage modification

Supplementary materials

Title
Description
Actions
Title
supporting information
Description
General information, experimental procedures, new com-pound characterization, crystallographic data, spectroscopic data, and NMR spectra.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

Version History

Feb 15, 2022 Version 2

Version Notes

One of our recent relevant work was cited and discussed to support the conclusion of this work, see ref 13.

Metrics

1,750
1,073
0
Views
Downloads
Citations

License

CC logo
CC
BY logo
BY
NC logo
NC
The content is available under CC BY NC 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-xl67g-v2
D O I: 10.26434/chemrxiv-2021-xl67g-v2 [opens in a new tab]

Funding

National Natural Science Foundation of China
22022114, 21971261
Guangdong Basic and Applied Basic Research Foundation
2020A1515010624

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

Share