Please use this identifier to cite or link to this item:
Authors: Beck, Alexander D.
Haufe, Stefan
Waldvogel, Siegfried R.
Title: Boron-catalyzed electrochemical Si−C bond formation for safe and controllable benzylation and allylation of hydrosilanes
Online publication date: 30-Jan-2023
Year of first publication: 2022
Language: english
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: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
Information on rights of use:
Journal: ChemElectroChem
Pages or article number: e202200840
Publisher: Wiley-VCH
Publisher place: Weinheim
Issue date: 2022
ISSN: 2196-0216
Publisher DOI: 10.1002/celc.202200840
Appears in collections:DFG-491381577-H

Files in This Item:
  File Description SizeFormat
boroncatalyzed_electrochemica-20230127155618790.pdf4.82 MBAdobe PDFView/Open