Autoren:	Beck, Alexander D. Haufe, Stefan Waldvogel, Siegfried R.
Titel:	Boron-catalyzed electrochemical Si−C bond formation for safe and controllable benzylation and allylation of hydrosilanes
Online-Publikationsdatum:	30-Jan-2023
Erscheinungsdatum:	2022
Sprache des Dokuments:	Englisch
Zusammenfassung/Abstract:	The range of possible applications of B(C6F5)3 extends into many areas of organic and inorganic chemistry. However, electrochemical synthesis with hydrosilanes using B(C6F5)3 to increase yield or scope has not yet been achieved. A comprehensive study on the use of Lewis acidic boron species, especially B(C6F5)3, 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(C6F5)3 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(C6F5)3 activated the hydrosilane for easier nucleophilic access, leading to significant increase in yield and enrichment of the target product in the reaction mixture.
DDC-Sachgruppe:	540 Chemie 540 Chemistry and allied sciences
Veröffentlichende Institution:	Johannes Gutenberg-Universität Mainz
Organisationseinheit:	FB 09 Chemie, Pharmazie u. Geowissensch.
Veröffentlichungsort:	Mainz
ROR:	https://ror.org/023b0x485
DOI:	http://doi.org/10.25358/openscience-8696
Version:	Published version
Publikationstyp:	Zeitschriftenaufsatz
Nutzungsrechte:	CC BY-NC-ND
Informationen zu den Nutzungsrechten:	https://creativecommons.org/licenses/by-nc-nd/4.0/
Zeitschrift:	ChemElectroChem 9 17
Seitenzahl oder Artikelnummer:	e202200840
Verlag:	Wiley-VCH
Verlagsort:	Weinheim
Erscheinungsdatum:	2022
ISSN:	2196-0216
DOI der Originalveröffentlichung:	10.1002/celc.202200840
Enthalten in den Sammlungen:	DFG-491381577-H