Boron‐Catalyzed Electrochemical Si−C Bond Formation for Safe and Controllable Benzylation and Allylation of Hydrosilanes
- Publication type:
- Journal article
- Metadata:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>The range of possible applications of B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>3</jats:sub> extends into many areas of organic and inorganic chemistry. However, electrochemical synthesis with hydrosilanes using B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>3</jats:sub> to increase yield or scope has not yet been achieved. A comprehensive study on the use of Lewis acidic boron species, especially B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>3</jats:sub>, for the activation of hydrosilanes in presence of commercially available supporting electrolyte for Si−C bond formation was presented. The benzylation and allylation of hydrosilane species was successfully conducted in presence of catalytic amounts of B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>3</jats:sub> in yields up to 86 %. Screening of electrode materials revealed leaded bronzes as superior for cathodic conversion without contamination of the electrolyte by heavy metals. Supported by cyclic voltammetry studies, B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>3</jats:sub> activated the hydrosilane for easier nucleophilic access, leading to significant increase in yield and enrichment of the target product in the reaction mixture.</jats:p>
- Autoren
- Alexander D Beck
- Stefan Haufe
- Siegfried R Waldvogel
- DOI
- 10.1002/celc.202200840
- eISSN
- 2196-0216
- ISSN
- 2196-0216
- Ausgabe der Veröffentlichung
- 17
- Zeitschrift
- ChemElectroChem
- Sprache
- en
- Online publication date
- 2022
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/celc.202200840
- Datum der Datenerfassung
- 2023
- Titel
- Boron‐Catalyzed Electrochemical Si−C Bond Formation for Safe and Controllable Benzylation and Allylation of Hydrosilanes
- Ausgabe der Zeitschrift
- 9
Data source: Crossref
- Other metadata sources:
-
- Author's licence
- CC-BY-NC-ND
- Autoren
- Alexander D Beck
- Stefan Haufe
- Siegfried R Waldvogel
- Hosting institution
- Universitätsbibliothek Mainz
- Sammlungen
- DFG-491381577-H
- Resource version
- Published version
- DOI
- 10.1002/celc.202200840
- Funding acknowledgements
- Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - Projektnummer 491381577
- File(s) embargoed
- false
- Open access
- true
- ISSN
- 2196-0216
- Ausgabe der Veröffentlichung
- 17
- Zeitschrift
- ChemElectroChem
- Schlüsselwörter
- 540 Chemie
- 540 Chemistry and allied sciences
- Sprache
- eng
- Open access status
- Open Access
- Paginierung
- e202200840
- Datum der Veröffentlichung
- 2022
- Public URL
- https://openscience.ub.uni-mainz.de/handle/20.500.12030/8712
- Herausgeber
- Wiley-VCH
- Datum der Datenerfassung
- 2023
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2023
- Zugang
- Public
- Titel
- Boron-catalyzed electrochemical Si−C bond formation for safe and controllable benzylation and allylation of hydrosilanes
- Ausgabe der Zeitschrift
- 9
Files
boroncatalyzed_electrochemica-20230127155618790.pdf
Data source: OPENSCIENCE.UB