title: Alkyne-azide click reaction catalyzed by metallic copper under ultrasound.
abstract: This protocol is for the ultrasound (US)-assisted 1,3-dipolar cycloaddition reaction of azides and alkynes using metallic copper (Cu) as the catalyst. The azido group is a willing participant in this kind of organic reaction and its coupling with alkynes is substantially improved in the presence of Cu(I). This protocol does not require additional ligands and proceeds with excellent yields. The Cu-catalyzed azide-alkyne cycloaddition (CuAAC) is generally recognized as the most striking example of 'click chemistry'. Reactions involving metals represent the favorite domain of sonochemistry because US favors mechanical depassivation and enhances both mass transfer and electron transfer from the metal to the organic acceptor. The reaction rate increases still further when simultaneous US and microwave irradiation are applied. The US-assisted click synthesis has been applied for the preparation of a wide range of 1,4-disubstituted 1,2,3-triazole derivatives starting both from small molecules and oligomers such as cyclodextrins (CDs). Using this efficient and greener protocol, all the adducts can be synthesized in 2-4 h (including work-up and excluding characterization). Click chemistry has been shown to be able to directly link chemistry to biology, thus becoming a true interdisciplinary reaction with extremely wide applicability.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Universidad de Extremadura, Avenida de Elvas s/n, Badajoz, Spain.
authors.forename: Pedro
authors.initials: P
authors.lastname: Cintas
authors.forename: Alessandro
authors.initials: A
authors.lastname: Barge
authors.forename: Silvia
authors.initials: S
authors.lastname: Tagliapietra
authors.forename: Luisa
authors.initials: L
authors.lastname: Boffa
authors.forename: Giancarlo
authors.initials: G
authors.lastname: Cravotto
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000295:instrumentation / Q000379:methods*; D003300:Copper / Q000737:chemistry*; D014465:Ultrasonics
chemical_list: D000480:Alkynes; D001386:Azides; D003300:Copper