Activation and Functionalization of Organic Disulfides by Bis(Perfluoroalkyl) Complexes of Nickel(II)
The [(MeCN)<sub>2</sub>Ni-(R<sub>f</sub>)<sub>2</sub>] platform was used to study the oxidative addition of 8,8'-diquinolyl disulfide. The oxidative addition proceeds to afford [Ni-(R<sub>f</sub>)<sub>2</sub>(SR)<sub>2</sub>] intermediates, which then eliminate R<sub>aryl</sub>-S-R<sub>fluoroalkyl</sub> products through consecutive carbon-sulfur bond-forming steps. The high-valent states of the nickel complexes are required to reductively eliminate the cross-coupled product, and it was shown through stoichiometric reactions that both the singly and doubly oxidized states can trigger the S-C<sub>perfluoroalkyl</sub> bond forming reductive eliminations. These results show that such metal-mediated coupling reactions are viable and worthy of consideration in new methods development.
Authors
- Roger E. Cramer (ORCID: https://orcid.org/0000-0002-3934-3401)
- David A. Vicic (ORCID: https://orcid.org/0000-0002-4990-0355)
- Cherry Mae T. Ravidas (ORCID: https://orcid.org/0009-0006-5909-5878)
Institutions
- University of the Philippines Los Baños (PH)
- University of Hawaii System (US)
- California Institute of the Arts (US)
- Lehigh University (US)
Publication Details
- Journal
- Organometallics
- Published
- 2025-10-02
- DOI
- https://doi.org/10.1021/acs.organomet.5c00310
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94