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Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction

A rhodium-catalysed stitching reaction between 2-(silylethynyl)arylboronates and 2-(silylethynyl)aryl bromides has been developed for the synthesis of unsymmetric dibenzo[a,e]pentalenes. The introduction of appropriately sized silyl groups on the starting substrates led to a high crossover selectivi...

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Detalles Bibliográficos
Autores principales: Takahashi, Keisuke, Ito, Shingo, Shintani, Ryo, Nozaki, Kyoko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5304618/
https://www.ncbi.nlm.nih.gov/pubmed/28451153
http://dx.doi.org/10.1039/c6sc04560j
Descripción
Sumario:A rhodium-catalysed stitching reaction between 2-(silylethynyl)arylboronates and 2-(silylethynyl)aryl bromides has been developed for the synthesis of unsymmetric dibenzo[a,e]pentalenes. The introduction of appropriately sized silyl groups on the starting substrates led to a high crossover selectivity without using an excess amount of either substrate. The present stitching reaction could produce a variety of unsymmetric dibenzo[a,e]pentalene derivatives, including those with electronically different substituents on the fused benzene rings as well as heteroarene fused compounds. Desilylative halogenation was also demonstrated to synthesise the corresponding halogenated dibenzo[a,e]pentalenes, which can be used as building blocks for further chemical transformations.