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Synthesis 2011(15): 2397-2406  
DOI: 10.1055/s-0030-1260083
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Arylseleno-1,2,3-triazoles via Copper-Catalyzed 1,3-Dipolar Cycloaddition of Azido Arylselenides with Alkynes

Anna M. Deobalda, Leandro R. S. Camargoa, Manfredo Hörnera, Oscar E. D. Rodriguesa, Diego Alves*b, Antonio L. Braga*c
a Universidade Federal de Santa Maria, Departamento de Química, CEP 97105-900, Camobi, Santa Maria, RS, Brazil
b LASOL, Universidade Federal de Pelotas, Departamento de Química Orgânica, CEP 96010-900, Pelotas, RS, Brazil
Fax: +55(48)37216850; e-Mail: diego.alves@ufpel.edu.br;
c Universidade Federal de Santa Catarina, Departamento de Química, CEP 88040-900, Florianópolis, SC, Brazil
e-Mail: albraga@qmc.ufsc.br;
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Publikationsverlauf

Received 3 April 2011
Publikationsdatum:
21. Juni 2011 (online)

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Abstract

The use of organoselenium compounds in the copper-catalyzed Huisgen 1,3-dipolar cycloaddition of azido arylselenides with various alkynes is described. Arylseleno-1,2,3-triazoles are prepared in excellent yields via reaction of amino arylselenides with iso-pentylnitrite and trimethylsilyl azide, and subsequent copper-catalyzed 1,3-dipolar cycloaddition of the resulting azido arylselenides with alkynes. The cycloaddition is also performed under mild conditions with several azido arylselenides and phenylacetylene to afford the corresponding arylseleno-1,2,3-triazoles in good to excellent yields. This click chemistry protocol represents an efficient method to produce new selenium-nitrogen compounds.

Key words

organoselenium compounds - azides - click chemistry - 1,2,3-triazoles

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