One-Pot Synthesis of Terminal Alkynes from Alkenes

[EN] The direct synthesis of terminal alkynes from widely available terminal alkenes is an unmet challenge in organic synthesis. Here, we show that alkyl and aromatic terminal alkenes can be converted to the corresponding alkynes in a one-pot process consisting of a Ru-catalyzed dehydrogenative hydr...

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Detalles Bibliográficos
Autores: Bilanin-Artigado, Cristina, Singh, Amravati Shivaji, Martínez-Belenguer, Lluis, Leyva Perez, Antonio|||0000-0003-1063-5811
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universitat Politècnica de València (UPV)
Repositorio:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
Idioma:inglés
OAI Identifier:oai:riunet.upv.es:10251/209538
Acceso en línea:https://riunet.upv.es/handle/10251/209538
Access Level:acceso abierto
Palabra clave:Alkynes
Alkenes
One-pot reaction
Dehydrogenative hydrosilylation
Vinyl silane
Iodosobenzene
Ruthenium catalysis
Acetylene
Descripción
Sumario:[EN] The direct synthesis of terminal alkynes from widely available terminal alkenes is an unmet challenge in organic synthesis. Here, we show that alkyl and aromatic terminal alkenes can be converted to the corresponding alkynes in a one-pot process consisting of a Ru-catalyzed dehydrogenative hydrosilylation, followed by an oxidative dehydrogenative reaction of the vinyl silane intermediate, enabled by the combination of PhIO with BF3. This formal alkene dehydrogenation reaction with commercially available reagents and under mild reaction conditions gives access to terminal alkynes in a simple manner, including acetylene.