Electrochemical Dehydrogenative sp<sup>2</sup>-Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif
A novel polycyclic naphthalenone motif was obtained by electrochemical synthesis starting from naphthols. The process is solvent controlled, and the highly diastereoselective cyclization is due to a solvent cage. The direct, anodic dehydrogenative sp<sup>2</sup>-coupling was carried out by flow electrolysis. Ten derivatives containing this motif were synthesized in yields up to 88%, resulting in novel polycycles structurally similar to bioactive compounds like Daldionin, potentially exploring the bioactive profile.
Authors
- Julian Buchholz
- Siegfried R. Waldvogel (ORCID: https://orcid.org/0000-0002-7949-9638)
- Elisabeth K. Oehl (ORCID: https://orcid.org/0000-0003-3579-152X)
- Maximilian M. Hielscher (ORCID: https://orcid.org/0000-0003-4365-3557)
- Dieter Schollmeyer
- Simone L. Kuhn
Institutions
- Karlsruhe Institute of Technology (DE)
- Johannes Gutenberg University Mainz (DE)
- Max Planck Institute for Chemical Energy Conversion (DE)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-10
- DOI
- https://doi.org/10.1021/acs.orglett.4c03518
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- European Commission
- Deutsche Forschungsgemeinschaft
- H2020 Societal Challenges