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Unusual nuclear exchange within a germanium-containing aromatic ring that results in germanium atom transfer

The delivery of single atoms is highly desirable for the straightforward synthesis of complex molecules, however this approach is limited by a lack of suitable atomic transfer reagents. Here, we report a germanium atom transfer reaction employing a germanium analogue of the phenyl anion. The reactio...

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Detalles Bibliográficos
Autores principales: Nishino, Ryohei, Tokitoh, Norihiro, Sasayama, Ryuto, Waterman, Rory, Mizuhata, Yoshiyuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10382490/
https://www.ncbi.nlm.nih.gov/pubmed/37507362
http://dx.doi.org/10.1038/s41467-023-40188-y
Descripción
Sumario:The delivery of single atoms is highly desirable for the straightforward synthesis of complex molecules, however this approach is limited by a lack of suitable atomic transfer reagents. Here, we report a germanium atom transfer reaction employing a germanium analogue of the phenyl anion. The reaction yields a germanium-substituted benzene, along with a germanium atom which can be transferred to other chemical species. The transfer of atomic germanium is demonstrated by the formation of well-defined germanium doped molecules. Furthermore, computational studies reveal that the reaction mechanism proceeds via the first example of an aromatic-to-aromatic nuclear germanium replacement reaction on the germabenzene ring. This unusual reaction pathway was further probed by the reaction of our aromatic germanium anion with a molecular silicon species, which selectively yielded the corresponding silicon-substituted benzene derivative.