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Transition metal-free cross-coupling of furan ring with haloacetylenes

On the example of menthofuran, a naturally abundant compound, it has been shown for the first time that the furan ring can be readily cross-coupled with acylhaloacetylenes in the solid Al(2)O(3) powder at room temperature to afford the corresponding 2-ethynyl derivatives in up to 88% yield. The reac...

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Detalles Bibliográficos
Autores principales: Sobenina, Lyubov N., Tomilin, Denis N., Gotsko, Maxim D., Ushakov, Igor A., Trofimov, Boris A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127138/
https://www.ncbi.nlm.nih.gov/pubmed/32287432
http://dx.doi.org/10.1016/j.tet.2018.02.024
Descripción
Sumario:On the example of menthofuran, a naturally abundant compound, it has been shown for the first time that the furan ring can be readily cross-coupled with acylhaloacetylenes in the solid Al(2)O(3) powder at room temperature to afford the corresponding 2-ethynyl derivatives in up to 88% yield. The reaction represents a ring closing/ring opening process that includes reversible formation of the intermediate cycloadducts further producing acetylene derivatives with elimination of HHal.