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

Ryohei Nishino, Norihiro Tokitoh (), Ryuto Sasayama, Rory Waterman and Yoshiyuki Mizuhata ()
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Ryohei Nishino: Kyoto University, Gokasho, Uji
Norihiro Tokitoh: Kyoto University, Gokasho, Uji
Ryuto Sasayama: Kyoto University, Gokasho, Uji
Rory Waterman: University of Vermont
Yoshiyuki Mizuhata: Kyoto University, Gokasho, Uji

Nature Communications, 2023, vol. 14, issue 1, 1-7

Abstract: Abstract 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.

Date: 2023
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DOI: 10.1038/s41467-023-40188-y

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