Manganese-Catalyzed Oxazoline-Directed C–H Addition of Arenes to Unsaturated Polar Bond: Experimental and Computational Study
The direct C-H aromatic addition to unsaturated polar bonds using abundant metals such as Mn and Co is scarce, and it has been mainly limited to the use of pyridine as a directing group. In this work, we introduce for the first time the use of oxazoline as a more versatile motif for this transformation, which can be further derivatized in other functional groups. The proposed mechanism shows a base-assisted formation of an Mn-tricarbonyl as the active species in the catalytic cycle, in contrast to the most reported Mn-tetracarbonyl complex. The mechanism was validated by experimental and DFT studies.
Authors
- Sebastián Gallardo‐Fuentes (ORCID: https://orcid.org/0000-0002-5285-8434)
- Tomás Chávez-Vega
- Marcelo Vilches‐Herrera (ORCID: https://orcid.org/0000-0001-8282-8650)
- Ramiro Robles‐Henríquez
- Tamara Maldonado (ORCID: https://orcid.org/0000-0002-3863-3001)
- Susan Lühr (ORCID: https://orcid.org/0000-0003-0449-0601)
- Omar Jamis-Oliva
- Andrés F. Flor-López (ORCID: https://orcid.org/0000-0002-8705-5658)
Institutions
- National University of Tucumán (AR)
- Pontificia Universidad Católica de Valparaíso (CL)
- University of Chile (CL)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-15
- DOI
- https://doi.org/10.1021/acs.joc.5c01326
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00