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Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

[Image: see text] A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion–oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts....

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Detalles Bibliográficos
Autores principales: Shu, Xing-zhong, Zhang, Miao, He, Ying, Frei, Heinz, Toste, F. Dean
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4333587/
https://www.ncbi.nlm.nih.gov/pubmed/24730447
http://dx.doi.org/10.1021/ja500716j
Descripción
Sumario:[Image: see text] A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion–oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)–aryl intermediate is proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy.