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

Christopher J. Smedley, Marie Claire Giel, Andrew Molino, Andrew S. Barrow, David J.D. Wilson, John E. Moses

Research output: Contribution to journalArticleResearchpeer-review

45 Citations (Scopus)

Abstract

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-1H-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.

Original languageEnglish
Pages (from-to)6020-6023
Number of pages4
JournalChemical Communications
Volume54
Issue number47
DOIs
Publication statusPublished - 14 Jun 2018
Externally publishedYes

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