Bromide-Mediated Silane Oxidation: A Practical Counter-Electrode Process for Nonaqueous Deep Reductive Electrosynthesis

Avanthay, Mickaël E.; Goodrich, Oliver H.; Tiemessen, David; Alder, Catherine M.; George, Michael W.; Lennox, Alastair J. J.

Abstract

The counter-electrode process of an organic electrochemical reaction is integral for the success and sustainability of the process. Unlike for oxidation reactions, counter-electrode processes for reduction reactions remain limited, especially for deep reductions that apply very negative potentials. Herein, we report the development of a bromide-mediated silane oxidation counter-electrode process for nonaqueous electrochemical reduction reactions in undivided cells. The system is found to be suitable for replacing either sacrificial anodes or a divided cell in several reported reactions. The conditions are metal-free, use inexpensive reagents and a graphite anode, are scalable, and the byproducts are reductively stable and readily removed. We showcase the translation of a previously reported divided cell reaction to a >100 g scale in continuous flow.

Citation

Avanthay, M. E., Goodrich, O. H., Tiemessen, D., Alder, C. M., George, M. W., & Lennox, A. J. J. (2024). Bromide-Mediated Silane Oxidation: A Practical Counter-Electrode Process for Nonaqueous Deep Reductive Electrosynthesis. JACS Au, 4(6), 2220-2227. https://doi.org/10.1021/jacsau.4c00186

• Journal Article Type: Article
• Acceptance Date: May 17, 2024
• Online Publication Date: Jun 3, 2024
• Publication Date: Jun 24, 2024
• Deposit Date: Dec 12, 2024
• Publicly Available Date: Dec 12, 2024
• Journal: JACS Au
• Print ISSN: 2691-3704
• Electronic ISSN: 2691-3704
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 4
• Issue: 6
• Pages: 2220-2227
• DOI: https://doi.org/10.1021/jacsau.4c00186
• Public URL: https://nottingham-repository.worktribe.com/output/35735005
• Publisher URL: https://pubs.acs.org/doi/10.1021/jacsau.4c00186