Issue 35, 2018

1-Bromoethene-1-sulfonyl fluoride (1-Br-ESF), a new SuFEx clickable reagent, and its application for regioselective construction of 5-sulfonylfluoro isoxazoles

Abstract

A new fluorosulfonylation reagent 1-bromoethene-1-sulfonyl fluoride was developed (1-Br-ESF). This unique reagent possesses three addressable handles (vinyl, bromide, and sulfonyl fluoride) and has great potential to function as a tris-electrophile and as a sulfur(VI) fluoride exchange (SuFEx) clickable material to enrich the SuFEx tool cabinet. The application of this reagent for regioselective synthesis of 5-sulfonylfluoro isoxazoles has been realized through a [3+2] cycloaddition with N-hydroxybenzimidoyl chlorides. This practical protocol provides a general and direct route to functionalized isoxazoles possessing sulfonyl fluoride moieties.

Graphical abstract: 1-Bromoethene-1-sulfonyl fluoride (1-Br-ESF), a new SuFEx clickable reagent, and its application for regioselective construction of 5-sulfonylfluoro isoxazoles

Supplementary files

Article information

Article type
Communication
Submitted
05 Feb 2018
Accepted
04 Apr 2018
First published
05 Apr 2018

Chem. Commun., 2018,54, 4477-4480

1-Bromoethene-1-sulfonyl fluoride (1-Br-ESF), a new SuFEx clickable reagent, and its application for regioselective construction of 5-sulfonylfluoro isoxazoles

J. Leng and H. Qin, Chem. Commun., 2018, 54, 4477 DOI: 10.1039/C8CC00986D

To request permission to reproduce material from this article, 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 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