Brominated [20]silafulleranes: pushing the limits of steric loading

Bamberg, Michael; Gasevic, Thomas; Bolte, Michael; Virovets, Alexander; Lerner, Hans-Wolfram; Grimme, Stefan; Bursch, Markus; Wagner, Matthias

doi:10.1039/D3CC02142D

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Brominated [20]silafulleranes: pushing the limits of steric loading

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Bursch, Markus
Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Bamberg, M., Gasevic, T., Bolte, M., Virovets, A., Lerner, H.-W., Grimme, S., et al. (2023). Brominated [20]silafulleranes: pushing the limits of steric loading. Chemical Communications, 59(48), 7459-7462. doi:10.1039/D3CC02142D.

Cite as: https://hdl.handle.net/21.11116/0000-000D-4BA6-4

Abstract

Starting from the perhydrogenated silafullerane [nBu₄N][Cl@Si₂₀(SiH₃)₁₂H₈], treatment with BBr₃ leads to partially and exhaustively brominated clusters, [nBu₄N][Cl@Si₂₀(SiBr₂H)₁₂Br₈] (120 eq. BBr₃, room temperature, 30 min) and [nBu₄N][Cl@Si₂₀(SiBr₃)₁₂Br₈] (300 eq. BBr₃, 130 °C, 3 d). Perbromination is accompanied by a massively increased steric strain on the cluster surface, which explains why our approach achieves regioselective derivatization of the Si₃₂ framework when mild conditions are maintained. Partial Br/H exchange on [nBu₄N][Cl@Si₂₀(SiBr₂H)₁₂Br₈] (30 eq. iBu₂AlH, room temperature, 16 h) affords [nBu₄N][Cl@Si₂₀(SiH₃)₁₂Br₈].