Pd/C‐Catalyzed Hydrogenation of CF <sub>3</sub> ‐, CF <sub>2</sub> H‐, and CF <sub>2</sub> CO <sub>2</sub> Et‐containing Pyridines: A Robust Method for Highly Functionalized containing Piperidines
Et groups has been developed. Using an inexpensive heterogeneous Pd/C catalyst, diversely functionalized fluorinated piperidines were synthesized under air- and moisture-tolerant reaction conditions (37 examples, up to 98% yield) with good to high diastereoselectivity. Comprehensive NMR studies enabled full structural characterization of the synthesized fluorinated compounds. The synthetic utility of the methods was further highlighted by the gram-scale preparation of the fluorinated scaffolds and the synthesis of a trifluoromethylated analog of the antipsychotic drug melperone.
Authors
- Vincent Ferey (ORCID: https://orcid.org/0000-0003-4118-3707)
- T. Charvillat (ORCID: https://orcid.org/0000-0003-4181-4310)
- Muriel Sebban (ORCID: https://orcid.org/0000-0002-7907-1092)
- Tatiana Besset (ORCID: https://orcid.org/0000-0003-4877-5270)
- Hassan Oulyadi (ORCID: https://orcid.org/0000-0001-5813-1482)
- Marc Daumas (ORCID: https://orcid.org/0000-0001-6832-4915)
- Patrick Bernardelli
- Xavier Pannecoucke (ORCID: https://orcid.org/0000-0002-4598-7895)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Sanofi (France) (FR)
- Normandie Université (FR)
- Université de Rouen Normandie (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2026-06-30
- DOI
- https://doi.org/10.1002/anie.4352204
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Sanofi
- Agence Nationale de la Recherche