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Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles

[Image: see text] The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho–ortho′ coupling pattern were obtained with high selectivity. Further oxidation led to ortho′–ortho′ coupling to generat...

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Detalles Bibliográficos
Autores principales: Liu, Lei, Carroll, Patrick J., Kozlowski, Marisa C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4576935/
https://www.ncbi.nlm.nih.gov/pubmed/25590578
http://dx.doi.org/10.1021/ol503521b
Descripción
Sumario:[Image: see text] The first regioselective oxidative coupling of 2-hydroxycarbazoles is described. With a vanadium catalyst and oxygen as the terminal oxidant, dimers with an ortho–ortho′ coupling pattern were obtained with high selectivity. Further oxidation led to ortho′–ortho′ coupling to generate a tetramer, which provided insight that the atropisomerization barriers of the unsymmetrical biaryl bonds are much lower than expected.