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Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles

Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively a...

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Detalles Bibliográficos
Autores principales: Ye, Changqing, Li, Yajun, Zhu, Xiaotao, Hu, Shengmin, Yuan, Daqiang, Bao, Hongli
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6432612/
https://www.ncbi.nlm.nih.gov/pubmed/30996957
http://dx.doi.org/10.1039/c8sc05689g
Descripción
Sumario:Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively affording structurally diversified tetrasubstituted allenes under mild conditions. Mechanistic studies suggest that an allenyl radical might be involved.