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

• DOI: 10.1021/acs.orglett.6b02420
• Publication Date: 2016-09-13T11:05:35Z
• Authors: Brandon M. Cornali; Flora W. Kimani; John C. Jewett
• Keywords: Alkyne; Triazole; Diazonium Compounds

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 ion generation. To increase the utility this releasing chemistry an alkyne-containing triazabutadiene was synthesized. The copper-catalyzed azide–alkyne cycloaddition ("Cu-click") reaction utilized modify and shown nitrogen-rich triazabutadiene. One triazole products tethered fluorophore, thus enabling direct fluorescent labeling model protein.