Flash Communication: Cobalt-Catalyzed Asymmetric Hydrogenation of a Fluorinated Cyclobutenoic Acid Derivative
An enantioselective hydrogenation of a fluorinated cyclobutenoic acid derivative using both neutral cobalt(II) and cationic, bis(phosphine)-supported cobalt(I) precatalysts has been developed. With 2 mol % of [((S,S)-PhBPE)Co(η6-PhMe)][BArF4], complete conversion and >99% ee was obtained at ambient temperature, enabling a route for the preparation of an enantioenriched bis(difluoro)-substituted cyclobutane. Deuterium-labeling studies supported homolytic cleavage of H2 and established the unsaturated starting material was not isomerized under catalytic hydrogenation conditions.
Authors
- David K. Leahy (ORCID: https://orcid.org/0000-0003-4128-7792)
- Lauren N. Mendelsohn (ORCID: https://orcid.org/0000-0002-0596-6838)
- Connor S. MacNeil (ORCID: https://orcid.org/0000-0001-6434-8397)
- Ian W. Davies (ORCID: https://orcid.org/0000-0001-6936-5540)
- Matthew V. Pecoraro (ORCID: https://orcid.org/0000-0003-2583-5314)
- Paul J. Chirik (ORCID: https://orcid.org/0000-0001-8473-2898)
- Katherine L. Moffa (ORCID: https://orcid.org/0000-0001-9261-5181)
Institutions
- Princeton University (US)
- Biohaven Pharmaceuticals (United States) (US)
Publication Details
- Journal
- Organometallics
- Published
- 2025-10-28
- DOI
- https://doi.org/10.1021/acs.organomet.5c00366
- Citations
- 1
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.54