Cu-Click Compatible Triazabutadienes to Expand the Scope of Aryl Diazonium Ion Chemistry

Brandon M. Cornali, Flora W. Kimani, John C Jewett

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Triazabutadienes can be used to readily generate reactive aryl diazonium ions under mild, physiologically relevant conditions. These conditions are compatible with a range of functionalities that do not tolerate traditional aryl diazonium ion generation. To increase the utility of this aryl diazonium ion releasing chemistry an alkyne-containing triazabutadiene was synthesized. The copper-catalyzed azide-alkyne cycloaddition ("Cu-click") reaction was utilized to modify the alkyne-containing triazabutadiene and shown to be compatible with the nitrogen-rich triazabutadiene. One of the triazole products was tethered to a fluorophore, thus enabling the direct fluorescent labeling of a model protein.

Original languageEnglish (US)
Pages (from-to)4948-4950
Number of pages3
JournalOrganic Letters
Volume18
Issue number19
DOIs
StatePublished - Oct 7 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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