“Anti-Michael addition” of Grignard reagents to sulfonylacetylenes: synthesis of alkynes

In this work, the addition of Grignard reagents to arylsulfonylacetylenes, which undergoes an “anti-Michael addition”, resulting in their alkynylation under very mild conditions is described. The simplicity of the experimental procedure and the functional group tolerance are the main features of thi...

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Detalles Bibliográficos
Autores: Esteban, Francisco, Boughani, Lazhar, García Ruano, José L., Fraile Carrasco, Alberto, Alemán Lara, José Julián
Tipo de recurso: artículo
Fecha de publicación:2017
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/678220
Acceso en línea:http://hdl.handle.net/10486/678220
https://dx.doi.org/10.1039/C7OB00783C
Access Level:acceso abierto
Palabra clave:Anti-Michael addition
Grignard reagents
Synthesis of alkynes
Química
Descripción
Sumario:In this work, the addition of Grignard reagents to arylsulfonylacetylenes, which undergoes an “anti-Michael addition”, resulting in their alkynylation under very mild conditions is described. The simplicity of the experimental procedure and the functional group tolerance are the main features of this methodology. This is an important advantage over the use of organolithium at −78 °C that we previously reported. Moreover, the synthesis of diynes and other examples showing functional group tolerance in this anti-Michael reaction is also presented