Non-Innocent Role of Sacrificial Anodes in Electrochemical Nickel-Catalyzed C(sp <sup>2</sup> )–C(sp <sup>3</sup> ) Cross-Electrophile Coupling
Sacrificial anodes composed of inexpensive metals such as Zn, Fe, and Mg are widely used to support electrochemical nickel-catalyzed cross-electrophile coupling (XEC) reactions, in addition to other reductive electrochemical transformations. Such anodes are appealing because they provide a stable counter-electrode potential and typically avoid interference with the reductive chemistry. The present study outlines the development of an electrochemical Ni-catalyzed XEC reaction that streamlines access to a key pharmaceutical intermediate. Metal ions derived from sacrificial anode oxidation, however, directly contribute to homocoupling and proto-dehalogenation side products that are commonly formed in chemical and electrochemical Ni-catalyzed XEC reactions. Use of a divided cell limits interference by the anode-derived metal ions and supports a high product yield with negligible side product formation, introducing a strategy to overcome one of the main limitations of Ni-catalyzed XEC.
Authors
- Luana Cardinale (ORCID: https://orcid.org/0000-0001-9867-3593)
- Christopher Y. Bemis
- Gregory L. Beutner (ORCID: https://orcid.org/0000-0001-8779-1404)
- Shannon S. Stahl (ORCID: https://orcid.org/0000-0002-9000-7665)
- Daniel J. Weix (ORCID: https://orcid.org/0000-0002-9552-3378)
Institutions
- University of Wisconsin–Madison (US)
- Bristol-Myers Squibb (United States) (US)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-11-15
- DOI
- https://doi.org/10.1021/jacs.4c10979
- Citations
- 22
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 5.50
Funders
- National Science Foundation
- Bristol-Myers Squibb
- National Institute of General Medical Sciences