title: Apparent copper(II)-accelerated azide-alkyne cycloaddition.
abstract: Cu(II) salts accelerate azide-alkyne cycloaddition reactions in alcoholic solvents without reductants such as sodium ascorbate. Spectroscopic observations suggest that Cu(II) undergoes reduction to catalytic Cu(I) species via either alcohol oxidation or alkyne homocoupling, or both, during an induction period. The reactions involving 2-picolylazide are likely facilitated by its chelation to Cu(II). The highly exothermic reaction between 2-picolylazide and propargyl alcohol completes within 1-2 min in the presence of as low as 1 mol % Cu(OAc)(2).
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
authors.forename: Wendy S
authors.initials: WS
authors.lastname: Brotherton
authors.forename: Heather A
authors.initials: HA
authors.lastname: Michaels
authors.forename: J Tyler
authors.initials: JT
authors.lastname: Simmons
authors.forename: Ronald J
authors.initials: RJ
authors.lastname: Clark
authors.forename: Naresh S
authors.initials: NS
authors.lastname: Dalal
authors.forename: Lei
authors.initials: L
authors.lastname: Zhu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D020005:Propanols; D014230:Triazoles; D003300:Copper; C028255:propargyl alcohol