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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

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

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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

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