Tunable Preparation of α‐Aminoacyl Fluorides and α‐Fluoroamides via Base‐Induced Cascade Multiple‐Cleavage Processes from Bromodifluorohydrin Reagents and Amines
A concise strategy for the divergent synthesis of α‐fluoroamides and α‐aminoacyl fluorides is developed via multiple bond‐cleavage processes of 2‐bromo‐2,2‐difluoro alcohols in the presence of amines. The transformation proceeds under mild conditions, displays a broad substrate scope, and features operational simplicity. Mechanistic studies, supported by density functional theory calculations, suggest the involvement of a putative gem ‐difluoroepoxide intermediate that triggers a cascade of atom recombination events.
Authors
- Mauro Spennacchio (ORCID: https://orcid.org/0009-0000-9127-8451)
- Michael Andresini (ORCID: https://orcid.org/0000-0003-4523-8488)
- Giancarlo De Santis
- Renzo Luisi (ORCID: https://orcid.org/0000-0002-9882-7908)
- Marco Colella (ORCID: https://orcid.org/0000-0001-7673-5335)
- Rosa Purgatorio (ORCID: https://orcid.org/0000-0003-1002-5087)
- F. Lauria (ORCID: https://orcid.org/0000-0001-8621-8841)
- Andrea Maranzana (ORCID: https://orcid.org/0000-0002-5524-8068)
- Leonardo Degennaro (ORCID: https://orcid.org/0000-0002-2187-9419)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie des Substances Naturelles (FR)
- International University College of Turin (IT)
- University of Turin (IT)
- University of Bari Aldo Moro (IT)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2025-08-15
- DOI
- https://doi.org/10.1002/adsc.70083
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- European Commission
- Universita degli Studi di Bari Aldo Moro
- HORIZON EUROPE Framework Programme