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Journal Article

Aryl Silicon Nucleophiles in Bismuth Catalysis

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Faber,  Teresa
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Engelhardt,  Sophia
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cornella,  Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Faber, T., Engelhardt, S., & Cornella, J. (2025). Aryl Silicon Nucleophiles in Bismuth Catalysis. Angewandte Chemie International Edition, e202424698. doi:10.1002/anie.202424698.


Cite as: https://hdl.handle.net/21.11116/0000-0010-E6D5-A
Abstract
We present a catalytic protocol utilizing bismuth for the synthesis of aromatic fluorinated thiosulfones, showcasing a seminal example of aryl silicon nucleophiles in Bi catalysis. This catalytic process is enabled by a series of Bi-based organometallic transformations, including an unprecedented transmetalation of aryl silicates to Bi(III) complexes and the formal migratory insertion of sulfur dioxide (SO2) into the Bi-C bond. The protocol is compatible with a wide range of anionic and neutral Ar-Si compounds, including heterocycles. Stoichiometric investigations of individual organometallic steps provide strong evidence supporting a Bi-redox-neutral catalytic cycle.