Iron-Catalyzed C–H Alkylative Ring Openings of Oxabicyclic Alkenes
We report the iron-catalyzed C-H alkylative ring openings of oxabicyclic alkenes by chelation assistance. The method converted a broad family of benzamides into highly functionalized dihydronaphthen-2-ol derivatives, amenable to further synthetic transformations by removing the triazole directing group. Remarkably, the iron catalysis displayed complete chemo- and regioselectivities in converting oxabicyclic alkenes functionalized at the bridgehead carbons. Mechanistic investigations, by means of DFT calculations, fully elucidated the mechanism of the iron catalysis.
Authors
- Andrea Serafino (ORCID: https://orcid.org/0000-0002-7902-4392)
- Gianpiero Cera (ORCID: https://orcid.org/0000-0002-2702-282X)
- Andrea Secchi (ORCID: https://orcid.org/0000-0003-2467-7908)
- Cristian Pezzato (ORCID: https://orcid.org/0000-0002-6950-8967)
- Stefano Santoro (ORCID: https://orcid.org/0000-0003-0223-1489)
- Prof. Dr. Lutz Ackermann
- Erika Barocelli
Institutions
- University of Parma (IT)
- University of Padua (IT)
- University of Perugia (IT)
- German Centre for Cardiovascular Research (DE)
- University of Göttingen (DE)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-01-07
- DOI
- https://doi.org/10.1021/acs.orglett.5c04816
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00