A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4223-4225

  Appukkuttan, Prasad ^a   Dehaen, Wim ^a   Fokin, Valery V ^b   Van Der Eycken, Erik ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRIAZOLE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTALLIZATION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; SUBSTITUTION REACTION;

EID: 9444260351     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048341v     Document Type: Article

References (27)

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27. Typical Experimental Procedure. (ATTENTION: copper azides are shock-sensitive when dry. Care should be taken to remove traces of these compounds from the products by washing with basic ammonium citrate or dilute HCl). Benzyl bromide (0.170 g, 1.0 mmol), phenylacetylene (0.107 g, 1.05 mmol), and sodium azide (0.068 g, 1.05 mmol) were suspended in a 1:1 mixture of water and t-BuOH (1.5 mL each) in a 10-mL glass vial equipped with a small magnetic stirring bar. To this was added copper turnings (50 mg) and copper sulfate solution ( 1 M, 200 μL), and the vial was tightly sealed with an aluminum/Teflon crimp top. The mixture was then irradiated for 10 min at 125°C, using an irradiation power of 100 W. After completion of the reaction, the vial was cooled to 50°C by air jet cooling before it was opened. It was then diluted with water (20 mL), and precipitated product was collected by filtration and washed with cold water (20 mL), followed by 0.25 M HCl (10 mL), and finally with petroleum ether (50 mL) to furnish 3a as a white solid (0.219 g, 93%).