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Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO(2)) atmosphere under mild conditions. It was found that CO(2) could be incorporated at the diketone enolic OH position, whic...

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Detalles Bibliográficos
Autores principales: Tian, Ya-Ming, Wang, Huaiju, Ritu, König, Burkhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694347/
https://www.ncbi.nlm.nih.gov/pubmed/35059173
http://dx.doi.org/10.1039/d1sc06403g
Descripción
Sumario:We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO(2)) atmosphere under mild conditions. It was found that CO(2) could be incorporated at the diketone enolic OH position, which was key to enabling the cleavage of a C–O bond during the rearrangement of a cyclopropane intermediate. This method allows for the same-pot construction of two isomers of the high-value tetra-substituted furan scaffold. The synthetic scope and preliminary mechanistic investigations are presented.