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Synthesis 2009(20): 3527-3532  
DOI: 10.1055/s-0029-1216985
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© Georg Thieme Verlag Stuttgart ˙ New York

The Sequential Sonogashira-Click Reaction: A Versatile Route to 4-Aryl-1,2,3-triazoles

Krisztián Lőrincz, Péter Kele, Zoltán Novák*
Department of Organic Chemistry, Institute of Chemistry, Eötvös Loránd University, Pázmány Péter stny. 1/a, 1117 Budapest, Hungary
Fax: +36(1)3722909; e-Mail: novakz@elte.hu;
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Publikationsverlauf

Received 5 June 2009
Publikationsdatum:
03. September 2009 (online)

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Abstract

Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira­-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.

Key words

alkynes - azides - cycloadditions - copper - cross-coupling

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6

When TBAF was added before the azide, 9% diphenylbuta-diyne was formed as by-product in the reaction mixture. With the addition of azide before the TBAF, we were able to suppress the homocoupling of the in situ formed terminal acetylene in every tested solvent. In EtOH-CH2Cl2 solvent mixture the amount of the diphenylbutadiyne side product remained below 1%.