Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon

A one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalyzed azide-alkyne cycloaddition (CuAAC). High yields of the β-methylsulfanyl tria...

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Detalles Bibliográficos
Autores: Alonso, Francisco, Moglie, Yanina Fernanda, Radivoy, Gabriel Eduardo, Yus, Miguel
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2013
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/85826
Acceso en línea:http://hdl.handle.net/11336/85826
Access Level:acceso abierto
Palabra clave:TRIAZOLES
ALKENES
COPPER NANOPARTICLES
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:A one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalyzed azide-alkyne cycloaddition (CuAAC). High yields of the β-methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the methylsulfanyl group has been demonstrated through a series of synthetic transformations, including direct access to 1-vinyl and 4-monosubstituted triazoles.