Conclusive Evidence for an SN2-Si Mechanism in the B(C₆F₅)₃-Catalyzed Hydrosilylation of Carbonyl Compounds: Implications for the Related Hydrogenation

Conclusive Evidence for an SN2-Si Mechanism in the B(C₆F₅)₃-Catalyzed Hydrosilylation of Carbonyl Compounds: Implications for the Related Hydrogenation

Just ask silicon: An experimentally straightforward yet effective Walden‐type analysis showcases the usefulness of silanes with a stereogenic silicon center as stereochemical probes. The B(C6F5)3‐catalyzed hydrosilylation and likely the related hydrogenation proceed through linear B‐H‐Si‐O transitio...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-07, Vol.47 (32), p.5997-6000
Hauptverfasser: Rendler, Sebastian, Oestreich, Martin
Format: Artikel
Sprache:eng
Schlagworte:
hydrosilylation
Lewis acids
nucleophilic substitution
reaction mechanisms
silicon
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Zusammenfassung:Just ask silicon: An experimentally straightforward yet effective Walden‐type analysis showcases the usefulness of silanes with a stereogenic silicon center as stereochemical probes. The B(C6F5)3‐catalyzed hydrosilylation and likely the related hydrogenation proceed through linear B‐H‐Si‐O transition states, as verified by flawless inversion of the absolute configuration at silicon (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200801675