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Ring-Opening Fluorination of Isoxazoles

01 April 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A ring-opening fluorination of isoxazoles has been developed. By treating isoxazoles with an electrophilic fluorinating agent (Selectfluor®), fluorination followed by deprotonation leads to tertiary fluorinated carbonyl compounds. The present method features mild reaction conditions, good functional group tolerance, and simple experimental procedure. Diverse transformations of the resulting α-fluorocyanoketones were also demonstrated, furnishing a variety of fluorinated compounds.

Keywords

fluorination
isoxazoles
fluorocyanoketones
ring-opening fluorination

Supplementary materials

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Supporting Information
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Experimental procedures and spectroscopic data for compounds including 1H, 13C, 19F NMR spectra (PDF)
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Now Published

Ring-Opening Fluorination of Isoxazoles [opens in a new tab]
Masaaki Komatsuda, Hugo Ohki, Hiroki Kondo, Ayane Suto, Junichiro Yamaguchi journal article
Organic Letters , Volume 24, Issue 17
Online publication date: Apr 26, 2022

Version History

Apr 01, 2022 Version 1

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

DOI

10.26434/chemrxiv-2022-bj42g
D O I: 10.26434/chemrxiv-2022-bj42g [opens in a new tab]

Funding

Japan Society for the Promotion of Science
JP19H02726
Japan Society for the Promotion of Science
JP21H05213
Japan Society for the Promotion of Science
JP21K18966
Japan Society for the Promotion of Science
JP20J14905

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) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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