1-Bromoethene-1-sulfonyl fluoride () is another good connective hub for SuFEx click chemistry

We demonstrate 1,2-dibromoethane-1-sulfonyl fluoride (DESF) as a bench-stable and readily accessible precursor to the robust SuFEx connector, 1-bromoethene-1-sulfonyl fluoride ( BESF ). The in situ generation of BESF from DESF opens up several new reaction profiles, including application in the synt...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (47), p.62-623
Main Authors: Smedley, Christopher J, Giel, Marie-Claire, Molino, Andrew, Barrow, Andrew S, Wilson, David J. D, Moses, John E
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical synthesis
Ethers
Fluorides
Organic chemistry
Substitutes
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 demonstrate 1,2-dibromoethane-1-sulfonyl fluoride (DESF) as a bench-stable and readily accessible precursor to the robust SuFEx connector, 1-bromoethene-1-sulfonyl fluoride ( BESF ). The in situ generation of BESF from DESF opens up several new reaction profiles, including application in the syntheses of unprecedented 3-substituted isoxazole-5-sulfonyl fluorides, 1-substituted-1 H -1,2,3-triazole-4-sulfonyl fluorides, 2-amino-1-bromoethane-1-sulfonyl fluorides and 4-bromo-β-sultams in good to excellent yields. These new modules comprise a pendant sulfonyl fluoride handle, which further undergoes facile and selective SuFEx reactions with a selection of aryl silyl ethers to generate stable and useful sulfonate connections. 1,2-Dibromoethane-1-sulfonyl fluoride ( DESF ): a bench stable and readily accessible precursor to BESF for the synthesis of β-sultams, sulfonyl fluoride substituted isoxazoles, triazoles and Michael adducts with SuFEx-able pendant sulfonyl fluoride handles.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc03400a