De Novo Synthesis of α-Hydroxy Ketones by Gallic Acid-Promoted Aerobic Coupling of Terminal Alkynes with Diazonium Salts

An unprecedented metal-free direct preparation of unprotected α-hydroxy ketones from terminal alkynes under mild conditions with diazonium salts as the arene source and without the requirement of irradiation is described. The process is general and fully compatible with a wide variety of substitutio...

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Detalles Bibliográficos
Autores: Alcaide, Benito, Almendros, Pedro, Fernández, Israel, Herrera, Fernando, Luna, Amparo
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/161747
Acceso en línea:http://hdl.handle.net/10261/161747
Access Level:acceso abierto
Palabra clave:Alkynes
α-hydroxy ketones
Selectivity
Synthetic methods
Metal-free reactions
Descripción
Sumario:An unprecedented metal-free direct preparation of unprotected α-hydroxy ketones from terminal alkynes under mild conditions with diazonium salts as the arene source and without the requirement of irradiation is described. The process is general and fully compatible with a wide variety of substitution in both reactants. Experimental and computational evidence strongly suggest the involvement of radical species in the transformation.