title: Copper(I)-catalyzed cycloaddition of bismuth(III) acetylides with organic azides: synthesis of stable triazole anion equivalents.
abstract: Fully loaded: Readily accessible and shelf-stable 1-bismuth(III) acetylides react rapidly and regiospecifically with organic azides in the presence of a copper(I) catalyst. The reaction tolerates many functional groups and gives excellent yields of the previously unreported 5-bismuth triazolides. This uniquely reactive intermediate is functionalized under mild reaction conditions to give fully substituted 1,2,3-triazoles.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037 (USA) http://www.scripps.edu/fokin.
authors.forename: Brady T
authors.initials: BT
authors.lastname: Worrell
authors.forename: Shelby P
authors.initials: SP
authors.lastname: Ellery
authors.forename: Valery V
authors.initials: VV
authors.lastname: Fokin
mesh_terms: D001386:Azides / Q000737:chemistry*; D001729:Bismuth / Q000737:chemistry*; D002384:Catalysis; D002414:Cations, Monovalent / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D009942:Organometallic Compounds / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001386:Azides; D002414:Cations, Monovalent; D009942:Organometallic Compounds; D014230:Triazoles; D003300:Copper; D001729:Bismuth
keywords: bismuth; click chemistry; copper; cycloaddition; heterocycles